


The Circle

by Snailhair



Series: Purpose [8]
Category: Supernatural
Genre: Angst, Character Growth, Crobby - Freeform, Daddy Issues, Destiel - Freeform, Family Issues, Fluff, Heart-to-Hearts, Humor, John's Journal, Jollie, Judence, M/M, Magic, Proposals, Romance, Sabriel - Freeform, Smut, family business, learning to let go of the past
Language: English
Status: Completed
Published: 2018-09-12
Updated: 2018-12-07
Packaged: 2019-07-11 07:00:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 13
Words: 72,567
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15967130
Author URL: https://archiveofourown.org/users/Snailhair/pseuds/Snailhair
Summary: When a dark character emerges from Crowley's past and threatens to toy with their family, the Winchesters ban together to hunt him, and help each other learn that history doesn't always have to repeat itself.





	1. Chapter 1

**Author's Note:**

> *** Before You Read*** Please know that this fic is a continuation of the “Purpose” series. If you have not read at least some of that story, most of this one will probably be confusing to you. Granted, the entire “Purpose” series is a long-haul read, but (probably) worth the trouble. However, if you wish to start reading here, you are totally free to do so! After all, we're all on 'Team Free Will', right? ;D Either way, I appreciate you giving this story a chance! :) … And to those of you who already know these stories and characters by heart: I really hope you enjoy this new addition! I've missed you all so much, and I just couldn't wait to share this with you! :) Now, onward to the overwhelming fluff!! XD

Being a Hunter wasn't so bad.

Chasing monsters, using weapons, drawing traps, reading Latin, helping ghosts cross over – all of that stuff was fairly simple. And sometimes kind of enjoyable. Like the time a little girl's spirit needed help finding the light, or when another set of Hunters invited the Winchesters to join them in taking down a huge vampire nest up in Washington. Jude liked being able to go out and 'take care of business,' Winchester style. It was part of who he was; a valuable piece of his whole self. Being a Hunter – being just like _his Dad_ – made Jude very happy.

But talking to people? Interviewing strangers for cases, while wearing an uncomfortable suit? Not so much...

Jude always hated being the center of attention. He hated the spotlight that shined on him when he had to speak to someone new. Even though he was twenty-one years old now, Jude was still as shy as his younger self. Talking to strangers wasn't his strongest attribute. And unfortunately, at the moment, Jude found himself doing just that. He was standing next to his uncle Sam in a stranger's house, shifting around ever so slightly to relieve the itch of his fancy clothing, feeling his own face filling with heat the longer eyes were on him. Luckily, uncle Sam was doing all of the talking, but that didn't stop the interviewee from staring boldly at Jude. And Jude struggled to keep his own discomfort to a discrete minimum as time dragged on...

“Ms. Porter, you mentioned that there was a strong odor,” Sam reminded, “Could you describe it?”

The lady blinked at Jude a few more times, making the heat rise quicker on his cheeks, before answering Sam's question.

“Uh, like rotten eggs. Or a... sewage plant,” she admitted with disgust.

“Like sulfur, maybe?” Sam suggested.

“Y – yes. It was coming from the body bag,” the lady nodded, “Is that... helpful?”

“Yeah, actually, it's very helpful,” Sam smiled graciously, suddenly rising to his feet, “We appreciate you giving us your time. I think Agent Kent and I covered everything we needed to, and we'll have to get going. If you remember anything else, please let us know.”

As Sam handed the lady a business card, Jude gulped and quickly scrambled to his feet to follow his uncle – which caused him to accidentally kick the coffee table. Jude immediately blurted a string of apologies as he straightened the furniture and turned away sheepishly. His face felt like a furnace of embarrassment. Ugh! He was messing up the whole interview! Jude just wanted to disappear from the room and never show his face in public again. But even though he had the ability to fly, he couldn't lift a wing as long as the lady was staring at him.

“Um... Sure,” she mumbled, glancing strangely between the coffee table and Jude.

Sam gave her a polite wave before leading the way outside. And Jude was right on his uncle's heels, ready to get as far away from the uncomfortable room as possible. The two of them didn't look back as they made their way to the Impala. _Jude's_ Impala. Her dark blue paint and chrome rims glistened invitingly in the sunlight, silently reminding him that a welcoming space was just within arm's reach. When Jude opened the driver's side door and sat down, he took the deepest breath he could muster, filling his lungs with the sweet scent of home. The warm atmosphere took away some of his embarrassment, but didn't quash it completely. Man, he just wasn't cut out for this 'interview' business... Jude put the key in the ignition and started up his car just as uncle Sam sat down in the passenger seat.

“It's alright, Jude. Calm down. I thought you did pretty well this time,” he complimented lightly as he shut the door.

Jude turned to give his uncle an utterly flat look. Pretty well? Who was Sam trying to fool?

“Can we just go home, now?” Jude nearly pleaded.

Sam chuckled a little, probably because he found Jude's discomfort amusing for some reason.

“Well, I was planning to talk to the store manager and find out if he saw anything,” Sam admitted, making the horror flash on Jude's face, “But I guess it can hold off until tomorrow.”

Jude sighed with relief and muttered 'thank you,' before carefully backing out of 'Ms. Porter's' driveway and heading toward the interstate that would carry him home, to the bunker.

It wasn't that Jude didn't like strangers. He didn't mind being out in the world with other people. It was the part where he had to _speak_ that wasn't so fun. Jude didn't know how his fathers and uncles became so comfortable with chatting to others; how they could effortlessly start a conversation – or even threaten someone – with ease. They were all so good at it. Hell, uncle Gabe was a freaking pro. Why didn't any of that charming charisma get passed down to Jude? Which 'Hunting' class did he miss?

Though he was fairly upset by his own latest social blunder, Jude focused his attention on the road and tried to think of better things. Of course, the immediate thought that popped into his head was his beautiful, half-demon boyfriend, Clarence. Jude hadn't seen Clarence in person for at least two weeks, mostly because Clare was working hard at Bobby's salvage yard up North and Jude had been busy figuring out this case with his family. They texted each other every day, but sometimes that wasn't enough. Jude wanted to hold him; to hug him, kiss him, and smother him with unbridled affection... but Jude knew those sweet moments would have to wait until their work was done. Saving up all that love for later didn't seem so bad. He just wished that 'later' would come sooner...

Driving through Lebanon seemed to make Jude's anxiety finally subside. When his blue Impala passed by Ms. Jane's dress shop, Jude and Sam both made sure to wave out the window. The lovely Latino Lady inside – Jude's best friend Ollie's mom – looked up just in time to see them and toss her own hand up with a smile. Seeing Ms. Jane made Ollie return to Jude's mind as well. He hadn't seen Oliver in a long time, either. Between attending college classes, working at a local animal shelter, and spending time with his own dad at the batting cages, Ollie didn't have time to hang out with Jude much anymore. Jude couldn't blame the guy, of course. School and work were important things. But, man, sometimes Jude wished that he could still see Ollie almost every day. They were practically brothers and Jude missed him a lot. Jessica was so lucky. At least she got to see him every now and then.

When Jude's Impala finally rolled up to the bunker garage, the twenty-one year-old nephilim let out a long sigh. Great. He had accidentally made himself upset again by thinking about the people he missed. Now, as he rolled into the silent garage and parked his car next to his dad's, Jude somehow felt worse than before. Man, why did people have to get so busy all the time? Why did life have to get so much harder as time went on? Why couldn't things just stay as joyful as they were during his childhood?

“You okay?”

Jude gulped as he looked up at uncle Sam next to him. At first, Jude didn't know how to answer. If he said 'yes', Sam would know that he was lying. But if he said 'no,' he would have to explain himself. Neither option sounded very appealing.

“Just...” Jude shrugged. He didn't know how to finish the sentence.

Surprisingly, a flicker of a grin appeared on Sam's mouth. He instantly bit it down and nodded, but Jude was able to see that he was hiding humor.

“I know,” he sighed, reaching over to pat Jude's shoulder, “It's been a long day. But you never know. Things could get better.”

Jude subtly glanced at his wristwatch. It was already six o'clock. If things were going to get better, they needed to hurry up... Jude only nodded to acknowledge his uncle's bland encouragement. As the younger Winchester opened the door to get out, the older remained seated with his laptop.

“You go on ahead, Jude. I'll, uh, catch up,” he called.

“Okay,” Jude mumbled.

He shut the driver's side door, which made the sound echo around the giant room, and shuffled toward the hallway that led to the rest of the bunker. He really hoped that his parents saved him some food from dinner. He couldn't smell any food yet, but he could feel his stomach rumbling.

Just as Jude took a step into the hallway, all the lights in the bunker went out.

Jude gasped and jumped, realizing that his vision was completely compromised. What happened? Did the power go out? Just as Jude was about to call for his uncle, he caught sight of a faint blue glow. It was coming from the floor just ahead, drawing his eyes forward again. It was a candle on the right side of the hallway, but the flame was solid blue. It flickered and swayed around a little like it was dancing, casting the cool glow on the floor. Where did _that_ come from?

Jude took a small step closer toward the odd candle, hoping to figure out what it was doing there, and another blue flame suddenly started to shine. It was a second candle, positioned on the other side of the hallway a little further up. Jude's eyes narrowed. Huh. Were these candles motion-activated or something? Why were they here in the bunker? Was aunt Rowena here, doing a spell or something? Just as Jude suspected, another candle lit as he took a step forward. By the time he reached the fourth candle, Jude heard something faintly echoing down the hall.

It was a guitar.

The little hairs on the back of Jude's neck stood on end. Holy shit. That was _Clare's_ guitar. Was Clare here? In the bunker?! Jude gulped and felt his feet pick up speed. As he walked, more and more blue candles sprang to life, lighting the way with the most gorgeous illumination he had ever seen. The closer he got to the end of the hall, the more Jude recognized the melody playing. It was a slow, sweet, acoustic version of “Across the Universe” by the Beatles. The louder the song grew, the more tears threatened to fill up Jude's eyes. God, that sounded so _beautiful_. What the heck was happening?

When Jude finally reached the end of the hall, he slowly stepped up inside the control room of the bunker and paused to take in the scene before him. The map table and the entire floor were dotted with those special blue candles, making the whole place beam with soft sapphire light. The ceiling, however, almost looked like outer space. It was twinkling with tiny stars and some kind of aurora borealis with a soft Lapis hue. And in the midst of this magical atmosphere, there was a blonde half-demon, gently strumming a guitar. It was Clarence. Clare was there, just like Jude hoped.

At first, Clare had his back to Jude and kept playing; gingerly plucking the strings as if he was caressing the guitar instead of playing it. It gave Jude a chance to realize that the guy was wearing a suit. An _actual_ suit. Jude had never seen him in a suit before, not even at Ollie's graduation. And, _damn_ , Clare looked so _good_ in a suit. When Clare finally turned around to face Jude, the nephilim was speechless. Jude only stood there with both hands over his open mouth, drinking in the breath-taking sight of his boyfriend dressed so handsomely. From the top of his blonde head, to the soles of his dress shoes, Clare was absolutely perfect. And that smirk! Ugh, that smirk was a true testament of the beauty of Grandpa Chuck's creation... Clarence eventually slowed the speed of his strums, bringing the sound low enough so that he could speak.

“There you are, Jaybird,” Clare grinned, his smile so soft in the cool light, “I was starting to think you and Bigfoot got lost.”

Jude only blinked. He _was_ lost. Lost in Clare's pretty eyes and his addictive melody... The demon played the song for a little longer, lowering his head to watch his own fingers dance along the neck of the instrument, before strumming the last cord and holding it for as long as he could. In the meantime, as the noise slowly faded away, he raised his head to smirk at Jude again.

“Eat your heart out, McCartney,” he muttered warmly.

Jude only let out a tiny chuckle behind his hands. He couldn't make words right now. Not while he was standing in the midst of this beautiful dream. After a few seconds, Clarence twisted his guitar around and let it hang on his back, which allowed Jude to soak in the front of Clare's outfit. He wasn't wearing a tie, which left the top few buttons of his white shirt undone, revealing the creamy skin of his Adam's apple and collar bone. Shit, Clare looked good in a suit. He needed to wear that more often.

“I hope this isn't too over-the-top for you,” Clare muttered, gesturing to the amazing room around them.

Jude was finally able to find his voice long enough to ask -

“Wh – what is this?”

It came out as a whisper, but Clare heard it. The handsome demon's smile grew as he made his way closer.

“This is you. And me,” he answered vaguely, “Sorta... This is the same room where we first met, remember?”

Jude nodded carefully. Yeah. He remembered the event in fine detail. Clarence was so sick and frail back then; so in need of love and care. But, why did any of that matter? Clare paused to look toward the staircase and point high up to the bunker's entrance.

“I wandered in through that door, high as hell, looking for anyone that would help me,” the demon recalled fondly, bringing his smirk back to Jude, “And then, out of nowhere, Superman shows up in full costume. Underwear on the outside and everything.”

Jude chuckled again, feeling himself beam with warmth at the memory. It was true. Jude really was dressed like Superman for Halloween all those years ago. Geez, it felt like ages.

“I never saw Superman shoot lasers out of his eyes, or stop a speeding bullet, or fly around the world so fast that he reversed time,” Clare mentioned, his eyes playing peek-a-boo with Jude's from under his long eye lashes, “but he does save my life. Every single day. If I didn't have Superman... If I didn't have _you_ , Jude... I would have died a long time ago.”

Jude gulped and reached out to touch Clare's warm cheek. He didn't like hearing Clare talk about himself like that. Jude hated the thought of anything bad happening to his love. Clare's hand rose up to cradle the back of Jude's, twisting it around to tenderly kiss the palm before bringing it down to hold. One more moment of silence ticked by in which Clare fiddled with Jude's fingers and smiled.

“Jay,” he whispered, looking back up into Jude's eyes, “I've made really shitty and horrible decisions in my life. I've made a ton of mistakes. I'm nowhere near perfect. I don't deserve anything good, let alone some one as kind, sexy, and loving as you... But, somehow, here you are. With me. I'm the luckiest son of a bitch on the planet... Or should I say, 'across the universe?”

Jude laughed again and tightened his hand around Clare's warm fingers. For the most part, he was very glad to hear all of these things, but part of him wondered where all of this was coming from. Why was Clarence saying all of these romantic things? While they stood close together, Clare took hold of Jude's free hand, too. He was clinging to both sets of Jude's fingers, still peering down into his eyes like he was seeing Jude's soul instead.

“I can't imagine what my life would have been like without you,” Clare admitted as he regained his playful smirk, “... and I can't imagine a future without you, either.”

A future? Did Clare think that Jude was going to leave him or something? Before Jude could open his mouth and tell Clarence that he wasn't going anywhere... the demon gradually lowered himself down. On one knee. Jude's heart suddenly flew into a panic, pounding so hard that he could feel it in his ears. Holy shit! Clare was down on one knee! Was he going to _propose_?! Clare's smirk burst into a full grown smile as he stared up at Jude from below.

“Jude Robert Winchester,” Clarence said boldly, letting go of one of Jude's hands to reach into his suit jacket pocket, “My Superman. My Jaybird. My guardian angel. My best friend. My whole universe...”

The demon paused again to bring his hand forward, revealing a tiny open box with a shiny ring inside. With his mouth agape, Jude blinked down at the jewelry, where his vision blurred with tears.

“I already belong to you. Mind, body and soul,” Clare nearly whispered, “And the only thing I want is to spend the rest of my life falling in love with you everyday... Jude, will you marry me?”

Jude could feel his own hands trembling inside Clare's, and could hardly see the guy's face through the tears in his own eyes. Holy crap! Yes! Yes, _of course_ Jude wanted to marry Clarence! He agreed with everything Clarence just said! But for a moment, Jude couldn't make the words come out. He was so stunned by everything that all he could do was stand there and blink down in shock at Clarence and the beautiful ring he was holding. The silence must have made Clare a little nervous, because his smile dimmed in the blue glow. But Jude quickly forced himself to start talking.

“Y – yes,” he croaked, feverishly nodding his head and making the tears slip down his cheeks, “Yes, Clare! _Yes_!”

Clare sighed – as if he had been holding his breath the whole time – and his smile returned at full power. The first thing he did was take the ring out of the tiny box, slip it onto Jude's left hand, and give it a quick kiss before standing back up to meet Jude's lips. Jude gave his boyfriend – his _fiance_ – the biggest, longest, most loving kiss he could muster, suctioning their mouths together like they were kissing for the first time. Jude had no idea how long it lasted before he pulled away to hug Clare. The nephilim practically buried his face into the demon's neck, holding him so tightly that he could practically feel his heartbeat.

Jude was in such a state of joy that he didn't notice applause until a few seconds later. Somewhere near by, there was clapping and shouts of congratulations. When Jude lifted his head to see where it was coming from he realized that the lights of the bunker had come back on – and his entire family was standing in the doorway that led to the Library, all clapping, whistling, and beaming with pride. The loud announcement of their presence made Jude blush. Wait, did they see the whole thing? Were they watching the whole time?

“I knew you'd say yes!” Jessica called with a grin as she discretely wiped away a tear of her own.

“Well done, Son. Proud of you,” Bobby winked to Clarence.

“Oh, our wee lamb is to be married!” Rowena cooed, “T'was a lovely speech, lad!”

“I'm just glad he didn't say anymore 'universe' jokes,” Uncle Gabe mentioned playfully.

“Hey. Give the kid a break. He did okay,” Jude's dad defended.

“Meh. I've heard better speeches at funerals,” Crowley purred, though he gave a secret wink.

“Oh, ha ha. You guys are sooo funny,” Clarence spat with a grin, “I thought I told you to wait in the kitchen.”

“You did. But we said, 'to hell with that' and watched anyway,” Gabriel shrugged.

“Should have known,” Clare mumbled with an eye roll.

“I, for one, feel humbled and honored to witness that beautiful event,” Papa said, stepping forward with honesty and glistening blue eyes, “Son, I... I am so very happy for you.”

Papa quickly reached out to momentarily pull Jude away from Clarence and into his own arms. Jude sighed inside his Papa's embrace, feeling a little better. Maybe it wasn't so bad that his family saw Clare's proposal after all.

“Thanks, Pop,” Jude muttered.

The rest of the family followed Papa's lead and walked into the control room to give Clare and Jude hugs. Dad and Jess both gave Jude big squeezes while Clare received one-armed hugs from Bobby and Crowley – and one giant cheek smooch from Rowena. Even Sam, who had somehow sneaked from the garage to the library without Jude's awareness, congratulated them as well.

“See? Told you your day would get better,” Sam smiled.

Jude only nodded and smiled. No wonder uncle Sam seemed so happy when they left that lady's house earlier. He probably knew about Clare's proposal all along. Jessie migrated her way back through the small crowd to get to Jude again, where she reached out to take his left hand.

“Aww, Jude, your ring is so beautiful!” she praised.

Jude took the time to actually look down at his new engagement ring, now that he could see it properly in the light. It was a silver band, kind of like his fathers' rings, but instead of the middle being laced with sapphires, it was lined with light blue-ish diamonds. Each stone glistened in the light as he turned his hand this way and that, shimmering like sunlight on water. It was absolutely breathtaking. Clare did a great job choosing the band.

“You're so lucky,” Jessica muttered.

Jude raised his head at the sound of underlying sadness in his cousin's voice. Though she appeared happy, Jude could tell that Jess was concealing woefulness. And Jude knew why. It was because, even though Jess and Ollie had been together practically their whole lives, Ollie still hadn't asked her to marry him. Remembering that fact actually made Jude feel surprised. Wow. He never would have guessed that he and Clare would be engaged before Jess and Ollie... How could he possibly make Jess feel better?

“Just think. You still get to look forward to your proposal,” Jude offered as kindly as he could, speaking low so no one else would hear.

Jessica gave him a small smile, but Jude could tell that his statement wasn't very effective. Poor Jess. She really wanted to get married to Ollie...

“Alright. Everybody to the garage. We're going out to celebrate,” uncle Gabe suddenly called.

“Goin' where?” Bobby asked.

“Somewhere with decent pie, I hope,” Dad mumbled.

“That Japanese steak house up the road,” Clarence called, “Don't worry. I'm buying.”

“Like Hell you are, boy. _I_ shall be covering the tab.” Crowley sneered, “No son of mine his going to waste money on such expensive 'food' on his engagement day.”

Bobby sighed dramatically from the back.

“Darlin', you can't pay for dinner with damned souls,” he gripped.

“Souls? No... I'll just make a deal with management,” Crowley corrected.

“Why can't we just have a normal, decent family dinner in public?” Sam asked as he followed the crowd down the hall.

“Because we're Winchesters. That's why,” Gabriel answered, “Now, give me your hoof, Moose-man. That proposal put me in a romantic mood.”

“Oh, God,” Sam grumbled, even though he offered his hand anyway.

As the crowd slowly moved toward the hall, Jude felt Clare's hand holding him back. It seemed like the demon was waiting for their family to get ahead of them so he could say something to Jude only. After Rowena disappeared around the corner, Clare finally brought his eyes back to Jude.

“Hey, Jay, I swear I didn't know they were watching. I told them to wait in the kitchen, 'cause I know how much you hate being stared at. I'm sorry,” he whispered.

Jude swallowed a large gulp, feeling his stomach flutter. Clarence knew him so well. Jude felt like he was married to him already...

“It's okay,” Jude promised, getting lost in Clare's eyes again, “I love you.”

Clare's smile lit up the whole room.

“I love you, too... Future husband,” he winked.

* * *

Dean picked up his drink and took another sip as he stared across the hibachi grill toward his adult son and soon-to-be son-in-law. Jude and Clarence were acting like star-crossed teenagers again, giggling and getting all handsy with each other. They were adorable as hell, but for some reason, it made Dean feel a little upset. It was probably just the lingering side effects of knowing his kid was an adult now and didn't need him anymore. Or maybe the oncoming emotions of knowing that he would literally have to give his son away at a ceremony in the future... But Dean tried his best to keep those problems to himself. This night belonged to Jude and Clare, and Dean wouldn't ruin it for the world.

Luckily, Cas seemed to be feeling the same way. The blue eyed angel only smiled a few times, and spent the rest of the dinner gazing at Jude with that forlorn, worried-mother look. Dean eventually sat his drink down and leaned over to comfort his anxious husband.

“Baby. It's gonna be alright,” Dean muttered in Cas's ear, just under the crowded ambiance of the restaurant, “Clarence is an okay kid. He'll take care of -”

“Jude is still our child, Dean,” Cas interrupted.

“Yes. He is,” Dean agreed, “and he always will be. But we can still share him with Clare. Jude loves him just as much as he loves us, you know.”

Cas finally turned his head to look at Dean, allowing him to see just how vividly emotional his sapphire eyes were. His soft lips, surrounded in scruff, pursed as he searched Dean's face.

“Very well,” the angel eventually allowed, lowering his head a bit, “... but if that demon does anything to hurt my precious son, torture will seem like a heaven-sent mercy compared to what I will do to him.”

Dean nearly choked on his drink and had to cough loudly, almost gaining the attention of several people at the table. Holy shit, Cas really meant business, didn't he? Thank God Clare was a good kid! Dean shook his head as he leaned back over to get near Cas's ear again.

“Geez, Cas. You need to lay off the serial killer documentaries,” Dean quipped, “From now on, Netflix is for chilling only, alright?”

Of course, Cas only turned back to give Dean that classic 'I do not understand' face. And it made Dean's stomach flutter with delight. God, he loved it when Cas made that face. It never got old.

Just as Dean reached out to pick up his drink again, he felt a hand on his shoulder. Both he and Cas turned to see Crowley hovering behind them. The nicely dressed King of Hell had been having just as much fun as everyone else at this party – until now. Now, his expression was completely serious. Dean couldn't remember the last time he saw Crowley without a smirk. Was everything okay?

“What?” Dean blurted.

“I need to speak with you. Alone,” he said, tossing a glance at Cas.

Dean briefly met eyes with his angelic husband, where they shared the same look of confusion. Crowley wanted to talk to Dean alone? That couldn't be good. Dean gave Cas a reassuring nod before climbing to his feet to join Crowley. The demon swiftly breezed through the crowded restaurant, leading Dean toward the restrooms at a brisk pace. Dean followed, but felt utterly lost. Oh God, did this have something to do with Jude and Clare getting engaged? Or maybe something about a case? Dean only hoped that Crowley was using the men's bathroom to have a private conversation and _not_ for its intended purpose, otherwise this was going to get uncomfortable fast.

When they entered the room, Crowley tossed out the only other guy in there – who happened to be standing at a urinal, and was forced to cover himself just before he was rudely excused from the bathroom – and locked the door behind him before turning to talk to Dean. His accented voice was low, but still echoed against the tiled walls when he spoke.

“Though it pains me to admit this, I... have a problem,” Crowley said.

Dean sighed. Ugh, he really hoped this wasn't a personal thing...

“Look, dude, if you're having bedroom troubles, I'm really not the guy your looking for,” Dean pointed out with disgust.

Crowley paused to dramatically roll his eyes and huff a breath.

“Oh, could you stow your adolescent humor for five bloody minutes?” the king growled, “This is a serious matter, you naive squirrel.”

“Alright. Fine. I'm all ears,” Dean sighed, “What is it?”

Crowley took another second to glance around before speaking again. This time, his voice was back to its original somber tone.

“My female demons are starting to go missing again,” he explained.

Dean narrowed his eyes and crossed his arms. Again? What did 'again' mean? Had some of Crowley's female demons gone missing before? As he stared at the King of Hell, Dean tried to remember if he heard Crowley mention it in the past. There was a vague memory attempting to surface, but for the life of him, he couldn't figure it out... until it finally dawned on him.

Back when Clarence first came to the bunker and they found Meg, she told them she had been kidnapped and raped. That was how Clarence came into existence; because some kind of serial-demon-raper knocked up Meg and left her to die, pregnant, on the side of the road. But when the Winchesters confronted Meg, Crowley informed everyone that he had killed her rapist years prior to that meeting. Clarence's dad, whoever the bastard was, was dead. At least, he was supposed to be. Was it possible that he was still alive?

And if he was alive... did he know that he had a son?

 

**Notes for the Chapter:**

> Guys. You have no idea. How much. I have missed you. *giant hugs filled with rainbows and sunshine* I just had one of the most frustrating summers of my life, and I cannot tell you how good it felt to finally sit down, write this first chapter, and give it to you! :D Yes, I've gone back to the 'Purpose' universe, but I couldn't help myself. My SPN bestie helped me come up with a few ideas and then, bam! A new story came into existence! :D I really hope you all haven't gotten tired of Jude and the gang yet, because there is still a lot of story ahead for them. (And lots of fluff. Some angst, but mostly the fluff. Lol.) :) As usual, I'm gonna try to post new chapters on Fridays (with the exception of this week.) Thank you all so much for reading! :) The next chapter will be out soon! :)


	2. Chapter 2

**Notes for the Chapter:**

> I just wanted to give you all a quick heads up that this chapter contains lots of fluffy, intense, steamy Judence smut. ;) Enjoy!

Dean continued to blink repeatedly at Crowley in the men's room for at least two solid minutes. It was still only the two of them, hunching closely under a florescent light next to the urinals. Their family was just outside, enjoying a nice meal amongst each others' company, but the hunter and the king of Hell were trapped together in haunting knowledge. The knowledge that Crowley's female 'employees' were being kidnapped and murdered. _Again_. And the only other time that happened was...

“Clare's father...” Dean eventually gained the motor function to say.

Crowley took a very large breath and exhaled slowly, shaking his head the whole time.

“If I had not killed him with my own two hands, I would agree with you,” the demon replied carefully, “but it simply cannot be the same bastard. The man responsible for all those missing girls in the past, including Meg's disappearance, met his fate in the desert. I slaughtered him like the dog he was and left his carcass for the vultures. Clarence's biological father has been dead for many years...”

“But you just said it's happening again,” Dean pointed out, “Female demons are going missing. Are you thinking that this is a copycat or something?”

Crowley was quiet for a second. His dark eyes flickered toward the metal stalls nearby and seemed to fill with uncertainty. Dean couldn't remember the last time he saw Crowley look so torn.

“It has to be,” he stated firmly, though his expression was perplexed.

Dean took a second to gather his own thoughts. It was clear that Crowley was positive that he killed Clare's dad, but what if there was a chance the guy survived? What if he was still out there, and responsible for this new wave of kidnappings? Where had he been this whole time? Crowley wasn't the type of guy that would half-ass a murder, especially if he was murdering someone responsible for messing with his 'workforce.' Maybe this _was_ a copycat. Maybe someone else was taking up the weirdo's mantle. Either way, there was only one thing that could answer all their questions.

“We've gotta catch this guy,” Dean said.

“No, we should let him roam free and continue his sadistic charade,” Crowley hissed sarcastically, finally looking back to Dean, “Of course we have to catch him! The faster we end this lunatic, the better... But there's another reason why I'm bringing this matter to _you_ first.”

Dean huffed a sigh. This couldn't be good...

“Why?” he asked.

Crowley tilted his head to look down and straighten out the hem of his suit jacket, but Dean could tell that he was finding a distraction so that he wouldn't have to look Dean in the eye when he spoke.

“Obviously, this situation will be very delicate for my s -” Crowley stopped short and coughed, “... for _Clarence_... So, until we have a confirmed identity on that worthless pile of cow dung, I would prefer that the boy remain unaware of this speculation. In fact, I believe it would be for the best if we not tell anyone about this conversation.”

“Okay,” Dean allowed gruffly, “but it sounds like you're gonna need all hands on deck if you want to catch this guy. How exactly are we supposed to keep this a secret from Bobby, Cas, Sam, and everyone else if you want their help?”

When Crowley raised his head to meet Dean's stare again, he was wearing his usual, pompous smirk.

“What? Don't tell me all these years of being married to Castiel have weakened your deceitful gift for lying,” Crowley challenged with an arched eyebrow.

Dean rolled his eyes. Really? Crowley thought he had to make a jab at Cas in order to make Dean comply? The balls on the guy...

“Fine. Whatever,” the hunter grumbled, “We'll just tell them that we're hunting some wizard who has a thing for demons or something. But as soon as we catch him, everybody gets to know the truth. _Everybody_ ,” Dean emphasized, thinking of Clarence, “Alright?”

“Yes, yes, alright. No need to twitch your fluffy tail at me, squirrel,” the demon scoffed, “I hope the lot of you can clear your schedule for the week. The most recent abduction happened in St. Louis and I have reason to believe he's still loitering around the area. I plan to capture the asshole there, tomorrow evening. With mother's help, we should be able to at least trap him.”

“And then?” Dean asked.

“Then I will properly dispose of that putrid filth,” Crowley answered coolly.

Dean nodded, but he knew what he had to say next.

“And if he turns out to be Clare's father?” the hunter prompted.

The fact that the guy might be related to Clarence seemed to upset Crowley just as much as it upset Dean. The demon looked back down and pondered on Dean's question for a second, eyes shifting between emotions.

“... Why should his relation to Clarence change my answer?” Crowley retorted, though his voice was terribly feeble.

“You know why,” Dean replied as gently as he could.

Though Crowley didn't say a word, they both knew the answer to that question. How could Crowley murder the father of the closest thing he'd ever had to a son? Sure, the guy was a raging, sadistic, psychopath. But didn't Clarence have a right to at least know who he was? They were blood. If things were the other way around – if Dean was in Clare's shoes – he would definitely want to meet his father. Or at least be offered the chance. Luckily, Crowley seemed to understand where he was coming from, because the demon sighed in defeat. But it wasn't enough to change his mind.

“This is all a moot point,” Crowley eventually spat, “The boy's father is already dead. And I will bury this new demon-snatcher right next to him... Are you going to help me or what, Winchester?”

Dean could tell that Crowley was trying to cover up his own fear; the fear that Clarence's father might still be alive, and that Clarence might actually want to meet him. But to keep things civil, Dean kept his comments to himself.

“Yeah,” Dean answered, “Now, can we get back to dinner?”

Crowley rolled his eyes, seeming perturbed by Dean's nonchalant attitude, but turned back toward the door.

“Do not speak to anyone about this 'father' business until the bastard is captured, Dean. Not even to that angel of yours,” Crowley warned as he walked, “Are we clear?”

“As clear as the tears of joy I'm gonna cry when we finally get out of this room,” Dean muttered.

Crowley appeared to accept Dean's sarcasm for honesty. The demon finally opened the door – where the man who Crowley tossed out of the men's room in mid-piss was walking out of the women's room. He kept his head down as he zoomed passed the demon and the hunter, probably too scared or embarrassed to look them in the eye.

On the way back through the savory-smelling restaurant, Dean's thoughts remained focused on the fact that Clare's dad might still be alive. When they eventually made it all the way back to their group at the hibachi grill, Dean found himself almost unable to look away from Clarence. The kid was still smiling and playing with Jude, blissfully unaware of all the things that Dean and Crowley were just talking about. It wasn't fair that they were keeping secrets from him, but it was probably for the best. At least for now.

As soon as Dean reclaimed his seat next to Cas, the angel immediately leaned over with frenzied blue eyes to look him over.

“Is everything alright, Dean? What happened? What did he say?” Cas asked in a panicked blur.

Before Dean could even open his mouth, he caught sight of Crowley's glare across the grill. The demon was obviously daring him to spill the beans. But, hey. Dean didn't take orders from Crowley. Especially when those orders involved not saying something to his angelic husband. Throughout their entire marriage, Dean never lied to Cas, and he wasn't about to start now. The restaurant they were in, however, was not the place to discuss it.

“Everything's okay, babe,” Dean promised, resting his hand on Cas's warm back, “I'll tell you all about it when we get home.”

* * *

“Okay. Which one of you morons ordered eight rounds of Sake and didn't tell anyone?” uncle Bobby growled, restaurant receipt in hand as he lead the way through the bunker.

A quiet snicker came from the back of the group and Jude turned around just in time to see uncle Gabe bury his grinning face into uncle Sam's side. The two of them were red faced and giggling, obviously a little drunk. The sight seemed to frustrate uncle Bobby, but Jude found it kind of sweet. He was glad that his family could share in the lovey-dovey feelings that he was experiencing. Jude and Clare might have been the ones who got engaged, but the celebration belonged to everyone.

“Balls,” Bobby hissed, “You idgits are lucky I had enough to cover the damn tab.”

“Sorry, Singer. I couldn't resist getting this moose a little tipsy,” uncle Gabe called as he patted Sam's arm.

“A little tipsy? The dude's stumbling around like a newborn deer,” Dad pointed out.

“I'm _not_ a queer!” uncle Sam suddenly slurred, bumping into the wall, “ _You're_ a queer! Ass-face!”

Nearly everyone chuckled at uncle Sam's misinterpretation of Dad's words, save Jess and Papa. Jess only shook her head and rolled her eyes, but Papa appeared a little confused and offended that uncle Sam would call Dad names. Uncle Gabe eventually pulled Sam further along.

“Yep. It's time to put this hammered caveman to bed,” he confirmed, “Nighty-night, you guys!”

As Gabe and Sam stumbled by, Jude stole a glance at the nearby clock on the wall. Oh man, it really _was_ time for bed. The thought of 'going to bed' made Jude really excited... and kind of nervous. Because he knew that tonight would be very special for him and Clarence, seeing as it was their engagement day. But Jude was nervous because he had been wanting to ask Clarence something for a very long time, and he hoped that Clare would finally agree...

“Uh, yo, Dean, Cas,” Clarence turned around to look at Jude's parents while holding Jude's hand, “Is it cool if I crash here tonight?”

Before Dad and Papa could even look at each other or open their mouths, uncle Crowley lunged forward to answer the question.

“Yes. Actually, we're _all_ going to stay the night,” he stated, turning to share a small look with Jude's parents and uncle Bobby, “There's a new case we're going to work on in the morning. Sorry I didn't tell you sooner, darling. It was all so sudden,” he paused to pat Bobby's arm, “... but yes. We will be staying in the bunker. And there are plenty of empty rooms to choose from, so take your pic, boy.”

“Oh, I'm staying in Jude's room,” Clare said boldly.

The mere mention of Jude and Clarence sharing a room made Papa's head snap toward them and his blue eyes to widen in fear. Jude cringed internally, letting his eyes fall to the floor. Oh, man, why did Clare have to be so blunt about things? Especially around Jude's parents?

“Um, that... that is not a very wise idea... because it... um,” Papa gulped, turning to grab Dad's arm, “Dean, will you explain to the children that its not wise for them to share rooms until -”

“Baby,” Dad interrupted in a comforting tone, “I hate to say it, but they're not kids anymore...”

Dad's statement seemed to hurt Papa more than anything. His mouth dipped open and he blinked in shock and pain. When his blue eyes fell back on Jude, Jude couldn't help but lower his head again in shame. Poor Papa. He still didn't like the thought of Jude being an adult.

“Don't worry, Pops. I'm gonna take reeeeally good care of him,” Clare promised with a smirk and a wink, playfully wiggling his fingers around inside Jude's hand.

Jude gasped and shoved his fiance's shoulder. Clare couldn't say that stuff to Papa and Dad! Did he want them to kill him?! From over the beaming red glare of his own cheeks, Jude could see that his parents were upset by what Clare said. Dad was giving him one of those 'are you kidding me?' looks, while Papa narrowed his eyes in suspicion.

“I do not like the tone in which he said that, Dean,” Papa leaned over to whisper to Dad.

Beside them, uncle Bobby and Crowley were exasperated by Clare's lack of discretion.

“Go. Now. Before I change my mind,” Crowley hissed.

Clare chuckled and gave their parents a tiny wave before pulling Jude down the corridor toward the bedrooms. Jude wished that there was something he could say to make Dad and Papa feel better, but he could only stutter a quick 'goodnight' as he shuffled along behind his fiance. Clare obviously wanted to 'go to bed' as much as Jude did...

When Clarence came to the familiar hallway that led into Jude's room, he nearly broke into a sprint. The change of pace made a laugh bubble out of Jude's smiling mouth. They were both inside Jude's room with the door shut in no time, surrounded by the soft glow of the Batman nightlight in the corner and the shelves full of books along each wall. Once they were alone, Clare tugged Jude close to hold him against his chest.

“I'm so glad you said yes,” the demon mumbled.

Jude nearly scoffed. How could he have said no? Clarence was his true love, just like Lois Lane and Superman. Jude raised his hand up to look at his new shiny ring again, admiring the way it sparkled in the gentle light of the room. Still, Jude couldn't pass up the opportunity to joke with Clare.

“The diamonds are kinda small,” Jude shrugged, even though they were massive, “but I guess it'll do.”

Clarence chuckled, knowing that Jude was poking fun at him.

“So sorry to disappoint you, future husband. I'll try harder next time,” Clare said, his eyes suddenly growing wide, “Oh, yeah. I almost forgot...”

The demon stepped away from the angel long enough to retrieve something from his pocket on his way toward one of the bookshelves. Jude watched closely as Clare reached way up high to put it in a certain place. It was his otter; one of the stuffed animals Jude gave him when they first met. Clare had brought it back to the bunker with him this time, and was now placing it next to Jude's otter. Once their little stuffed paws were close enough, they magnetically 'clicked' together. Jude beamed up at the pair of animals from below, feeling love and warmth swirl in his heart. Aw, the otters were reunited at last.

“There. Now they're together again, where they belong,” Clare smirked, turning around to stare fondly at Jude, “Just like you and me.”

Jude's heart nearly melted inside his ribcage. Ugh, that was so sweet. Today, Clarence was the best poet in the world. With his smile still intact, Clarence walked back over to Jude's open arms and met him with a kiss. This one tasted different than the first. It had a lot more heat – and a lot more tongue. The bonfire in Jude's chest, which always burned for Clarence, was slowly spreading to the rest of his body. This was it. Jude had been waiting for this since the moment he said yes...

“Mmm,” Clare hummed, pausing to shrug out of his suit jacket, “Is it hot in here, or is it just you?”

Jude smiled against Clare's moist lips. He didn't know why Clare felt the urge to flirt with him so much. Jude was already his.

“I already said yes, Clare. You don't have to keep using pick-up lines on me,” Jude pointed out as he slid out of his own suit jacket.

“That's true,” Clare smirked, “but speaking of picking you up...”

Jude gasped as he felt his feet lift from the floor. Clarence had leaned over, locked both his arms around Jude's backside, and lifted him up, causing Jude's hands to desperately cling to Clare's neck with the quick motion. The demon was all smiles as he carried the angel over to the bed and promptly laid him down on it. The sudden drop tickled Jude's stomach and made him laugh. Through the strands of Clare's shaggy blonde hair, his white teeth and pink lips were visible overhead.

“Hey, Jay,” he said, pausing to smother Jude's mouth with a another kiss, “Is it weird that we're about to have sex in your superhero sheets?”

Jude gulped. Wow. He never thought about that. But it did sound really dirty...

“Um... Well, I'm pretty sure we've done it before,” Jude reminded, thinking of that one time Clare sneaked into the bunker a few months earlier.

“Huh. I guess you're right,” Clare shrugged.

The handsome demon suddenly sat up, straddling Jude's waist so that he could finish taking off his shirt. Underneath him, Jude swallowed roughly again, feeling himself starting to harden in his own pants. Looking at Clarence's bare chest and tense stomach made him remember his thoughts from earlier. The two of them had sex regularly, but this time, Jude really wanted to try something they had never done before...

“Here you go, Superman,” Clare smirked, pulling his hand from his pocket to hold out a condom toward Jude, “Your rubber raincoat.”

Jude didn't move a muscle. He only blinked shyly at the condom before meeting Clare's eyes. Jude knew that Clarence was going to argue, but he had to try...

“Actually, Clare,” Jude muttered, his cheeks burning red again, “I was hoping that... that _you_ could wear it this time...”

There was an immediate shift in the room. Clarence's smile vanished and his eyes dulled, and it nearly broke Jude's heart. He really hated making Clare upset. Jude didn't want to make him uncomfortable with this subject, but he felt like they needed to at least talk about it.

In all the time they had been intimate with each other, Jude had always been the 'top'. There was nothing wrong with that, of course. Jude liked being inside Clare. He enjoyed gently thrusting into him and feeling the wet warmth of Clare's body around his own member. But Clarence never wanted to trade places. Not once. Jude was sure that it had something to do with Clare's past experiences, so he never brought it up, even though he desperately wanted to try being the 'bottom'... But tonight – their engagement night – Jude finally felt comfortable enough to make a stand.

Unfortunately, the idea upset Clare more than Jude thought it would. The demon huffed a breath of aggravation and crunched the wrapped condom in his hand, lowering his head and shaking it toward the wall.

“Jude, I've already told you. I'm not doing that,” he stated bluntly.

Jude could feel his own timid side wanting to surrender; to give up and let Clarence be the bottom like always. But his Superman side wasn't so easily swayed.

“Why are you so against it, Clare?” he gently pressed, caressing Clare's hips to comfort him, “I mean, I... I think we would both really enjoy -”

“No. We wouldn't.”

Before Jude knew it, Clare was climbing off of him and the bed completely; standing up near the bedside table to stare at the wall. Jude immediately spun around to sit on the edge of his bed. He wanted to reach out and touch Clare, to offer him some kind of affectionate gesture, but he was unsure if Clare would want to be touched right now. Jude felt so terrible. Maybe he shouldn't have brought it up. How could he explain himself?

“I'm sorry,” Jude almost whispered, “I just... I wanted to f – feel you inside me.”

Once again, Jude's face was on fire. He couldn't believe that he had said something so dirty out loud. Shame and discouragement were clashing in his heart, slowly washing out the arousal that had been growing there. God, he was so stupid. He ruined everything... Luckily, Clare eventually turned back around. He was still clutching the condom in a death grip, but his eyes had softened a little. The greenish-brown orbs flickered between Jude and the floor as he spoke.

“What you're asking for,” he began in a whisper, “is painful. Jude, taking a dick in the ass is not pleasant. Especially the first time. Believe me.”

“You let me do it to you all the time,” Jude interrupted.

“Yeah. Because I know what to expect. I'm used to it,” Clare argued, his voice calming to a whisper, “But you... you're... you're so...”

“Weak?” Jude offered frailly.

“No,” Clare instantly denied, his voice cracking, “You're so _innocent_ , Jay. God, you have no idea... You're so _important_ to me. I don't want to hurt you. Not that way. Not ever.”

Jude felt like he finally understood where Clare was coming from. It wasn't his past that prevented him from going that far with Jude – although, that may have been a contributing factor. It was how much he _loved_ him. Clare didn't want to 'top' Jude because he didn't want to hurt him. Somehow, that made Jude feel a little better.

Putting on his best smile, Jude stood up from the bed and reached out to take Clare's free hand. It was all tensed up, like he was full of anxiety, but his fingers willingly greeted Jude's.

“Clare,” he began, “This is going to sound weird, but I was literally _created_ that way.”

The idea of Jude's parents having sex must have made Clare uncomfortable, because an awkward smile flashed on his mouth.

“Wow. Thanks for bringing _that_ up. Bye-bye, erection,” he mumbled playfully toward his own pants.

“Sorry,” Jude said, scrunching his nose with a smile, “What I'm trying to say, is that it kind of runs in my family. I can do it, Clare. I _want_ to do it. We can go slow, take our time, and do it the right way. I promise I can take it. I trust you more than anyone. You could never hurt me... Future husband...”

The nickname he tacked on the end seemed to bring Clarence completely out of his doubt. He even glanced down at Jude's hand, where their engagement ring was still glistening in the soft glow of the nightlight. Afterward, he met Jude's stare and his defenses seemed to crumble. Clare let out a long sigh, which caused some of his messy blonde hair to sway around, but his grip on the condom loosened up and he looked down at it with a conquered expression.

“Fine,” he grumbled, raising his head to look Jude directly in the eyes again, “but if it hurts you, even a little bit -”

“Then we can do it the other way,” Jude agreed, feeling the smile burst across his own face, “Thank you, Clare! _Thank you_!”

“Don't thank me yet. I still have to work up a hard-on,” Clarence huffed, glancing at his own pants again, “Won't be much use, otherwise.”

“Oh, I can help with that,” Jude instantly volunteered.

The younger man stepped up to the older and slid his arms around him, welcoming him back into another steamy kiss. Jude's right hand timidly worked its way around to Clare's front, where it caressed the little trail of warm hair above his waist band. Clare hummed inside their kiss again, pulling back to sigh erotically.

“The beast only awakens for you, you know,” the demon purred.

Jude grinned wildly, feeling like a champion. It was nice to know that he was the only one Clarence had any sexual desire for. As they kissed again, Jude felt Clare gently nudge him toward the bed. In the meantime, Jude reached down to undo his own belt and pull down his pants and underwear along the way, revealing his own stirring beast. At the bed, Jude finally broke away from Clare and turned to climb onto it, staying on his hands and knees to position his backside toward Clare. A distinct hiss came from behind Jude, as if Clarence was exhaling heatedly.

“Holy shit,” the demon breathed, “I hope you've got plenty of lube...”

“Yeah. In the side table drawer,” Jude answered, furrowing his eyebrows, “Why?”

He could hear Clare rummaging around in the drawer to retrieve the lubricant as he waited for the answer.

“Because there's no way my dick's fitting in there unless I stretch you out first,” he answered.

Jude looked down at the Batman logo on the sheet beneath him, feeling worry creep into his chest. Stretch him out? Oh, boy. That sounded... painful. Even though he was a little intimidated, Jude forced himself to relax. He didn't want to upset Clarence, not after fighting so hard for this. _It's alright. You're Superman,_ Jude recited in his mind, _Clare will take care of you_. One of Clare's warm hands suddenly clutched his hip.

“Jay. I'm gonna slide a finger in first, okay? Just try to relax your muscles,” the demon instructed.

Jude nodded to show that he understood what to do. A few seconds later, one of Clare's wet fingertips circled the ring of Jude's hole and carefully slid inside. Jude bit his lip and held on tight to his bedsheets. Clare was right. It _did_ hurt a little. But not as much as Jude thought it would. Clarence was being so gentle; moving slow, prodding his finger against Jude's insides at a steady pace. And to top it all off, he was kissing Jude's back the whole time, pecking his spine with soft, loving lips. The sensation of Clare's mouth on his skin coupled with the motions taking place near his ass were starting to make Jude breathe faster. His scrotum and hardening shaft were dangling heavily between his legs, tensing with each thrust of Clare's fingers. Oh, man it felt so good...

“I'm gonna add another one,” Clarence warned.

When the second finger entered Jude's hole, he had to hold in a gasp. He felt so _full_ already. How could anything else fit in there? Surprisingly, Jude could feel his muscles loosening, just like Clare wanted. With a few thrusts of his fingers, the pain seemed to ease up. It might have had something to do with the fact that Clare's free hand was playing with Jude's swaying dick now, too. But either way, at least Jude was getting used to the bizarre feeling. In fact, it was starting to feel kind of good.

“Mmm,” Jude hummed aloud.

Clare's fingers suddenly flew out of Jude's hole, making the angel's eyes flutter open at the abrupt exit.

“What? Did I hurt you? I'm sorry, I was trying to go slow,” Clarence said in a blur, sounding so worried.

“N – No,” Jude said, turning on the bed to look at him properly, “I'm fine.”

“You sounded like you were in pain,” Clare pointed out in suspicion.

“No, I was enjoying it,” Jude explained, reaching back to pet his fiance's bare chest, “Please keep going, Clare.”

Although he seemed hesitant, Clare eventually nodded and picked up the bottle of lube. Jude smiled and returned to his original position, facing the sheets with his ass in the air. Clarence's newly moistened fingers returned to Jude's hole one at a time, easing in as slow as possible and thrusting carefully. The familiar motion made Jude ache with lust, but he held down his moans. He didn't want Clare to think he was in pain. It continued for a few minutes before Clare's fingers eventually slowed to a stop.

“Are you sure you're gonna be able to do this, Jude?” he asked quietly.

“Yes,” Jude answered, rocking his hips backward.

Clare sighed and slowly slid his fingers out again. Jude was about to ask what he was doing – when he felt the tip of Clare's erection rub against his entrance. Shock and arousal flooded Jude's system, making his hands clutch the superhero sheets even tighter. This was it! Clare was actually going to do it this time! He was going so slow; inching in little by little, filling Jude up to the max. Oh, God, it was so big! It felt so weird – and _amazing_!

“Ah!” Jude moaned.

As of on cue, Clare pulled himself out of Jude's hole and sighed again.

“Alright. You know what? You're gonna have to roll over or something, Jay,” he grumbled, “I can't tell if I'm hurting you or not. I need to see your face.”

Jude immediately complied with his fiance's request. He dropped down on the bed and rolled over on his back, keeping his legs spread apart so that Clare could gain access. Looking up at Clarence's naked body – and seeing his condom-covered erection standing at attention – made Jude nearly shudder. He loved this view so much. Luckily, Clarence seemed aroused by the sight of Jude's front also. His greenish-brown eyes danced along Jude's whole body before he finally stepped forward to reenter Jude's hole. The angel held his own legs back and stared up at the demon's face the whole time, mesmerized by his panting mouth.

“K – keep going,” Jude encouraged.

Clare's throat quivered with a gulp, but he pressed on, sliding so far into Jude that it caused another moan to erupt from the angel's open mouth. Shit! He was so _full_! The massive size was a little painful at first, but when Clare started to rock in and out, pleasure slowly started to take over. Clare was so focused on being careful that he didn't seem to be enjoying it very much. Jude reached up to cup the demon's handsome face as he worked, wanting to bring his attention back to the moment. And when their eyes met in mid-thrust, child-like vulnerability appeared in Clare's expression.

“Oh, no,” he breathed, sounding so frightened.

“Wh – what?” Jude asked, still holding onto his face.

Clarence panted a little, still rocking in and out of Jude at a steady pace. He rested and elbow on the bed next to Jude for leverage while his other hand stayed on Jude's thigh.

“I... I actually like this. More than I thought,” he admitted, seeming to let go of his earlier worries, “Oh, God. You feel so good, Jay...”

Jude finally let himself moan again, feeling so glad that Clare agreed.

“I like it, too,” he nodded feverishly, “Really, I do.”

Clare smirked as he thrust, breathing hard into Jude's face.

“Y – you're supposed to say that at the altar, remember?” he grinned.

Jude smiled back, feeling his heart swell with just as much love as the rest of his body. The thought of marrying Clarence – and being able to do this all the time, whenever they wanted – was almost overwhelming. Jude brought Clare's head down to kiss his lips for a moment before they broke apart to breathe. Jude could tell that the pleasure was building up between them. Clarence had sped up to a fast, even pace; thrusting so hard into Jude that the bed squeaked and his balls smacked against Jude's back. And Jude could feel his own scrotum tensing up between their grinding pelvises. He was nearing his own climax just like Clare.

“Ah, h – harder,” Jude pleaded.

Clare bit his lip and hammered down, fulfilling Jude's request with vigor. In between thrusts, Jude reached down to take hold of his own erection and stroke it in unison with each blow, knowing the end was on its way.

“Shit,” Clarence groaned, burying his face into Jude's shoulder as he held on with all his strength, “I'm... I'm gonna...”

“Me too,” Jude agreed, feeling pleasure radiate to every inch of his body, “Don't stop! Ah! Cl – _Clare_!”

A giant wave of ecstasy flooded Jude almost instantly. It was so massive that he barely felt the warm fluid splattering up his own stomach. All he could do was lay there and feel Clarence all around him; on his chest, between his legs, against his pelvis. Even Clare's scent was swirling in his lungs as he breathed. In all the times they had sex, Jude had never felt so close to Clarence. Having Clare inside him made all the difference in the world.

With a few muffled groans of his own, Clare appeared to come right after Jude. His hips thrust erratically and his arms trembled before he shuddered to a halt. Clare wasted no time removing himself from Jude's body. He slid out as soon as his orgasm was over, probably to keep from hurting Jude. But Jude wrapped his legs around Clare's waist so that he wouldn't completely roll away. He wanted to keep the demon close, so that they could cuddle in the sweaty aftermath of their latest accomplishment.

For a moment, they just laid there and panted, both too exhausted and mellow from their orgasms to fully think or speak. In fact, Jude was so blissful that it took him a second to realize that something was happening to his hand. He worked up the strength to look down and saw that Clare was pressing gentle kisses to his left hand – and to the engagement ring circled around his finger. A warm smile bloomed on the angel's face as he watched his fiance smother him in kisses. He was so happy that Clare enjoyed that as much as he did... The demon eventually looked up to meet Jude's eyes again.

“Damn,” he hummed, “I'm so glad you talked me into doing that.”

Jude chuckled, reaching a shaky hand down to comb some of Clare's blonde hair out of his pretty face.

“So am I,” he agreed.

* * *

When he was finally alone with his husband – in their bedroom, after everyone else had scampered off for the night – Dean told him about the entire conversation he had with Crowley. He included every little detail, including the bit about the poor guy who had to use the lady's room after Crowley tossed him out. And by the time he got to the end, Cas had that look of confusion and wonder on his face. The angel plopped himself down on the end of their bed and gazed through Dean, as if he was trying to make his own hypothesis.

“I see,” Cas breathed, “So, the person responsible for recently kidnapping demons... could be Clarence's biological father?”

Dean nodded as he tugged his shirt up over his head and started to undo his belt.

“Crowley says its not, but from the look in his eye, I'd say there's a chance,” he explained.

“But, I do not understand. Why would Crowley withhold this information from Clarence?” Cas asked, sounding genuinely concerned.

Dean paused again to step out of his pants and head for his side of the bed, where he rolled down the blankets.

“I think he's worried that Clare might want to meet the guy instead of just kill him,” Dean assumed, “but I don't know. All I know is that he told me not to tell anyone. So try not to mention it. Especially not to Clare or Jude.”

“Jude?” Cas repeated, turning around on the bed to tilt his head toward Dean, “Why wouldn't we tell our son about this, Dean?”

“For the same reason Crowley shouldn't have told me,” Dean replied as he laid back on the pillow to smile at his husband, “I love you more than anyone, so I tell you everything. And Jude loves Clarence...”

“So he would tell him as well,” Cas finished, bobbing his head with clarity, “I understand.”

Dean nodded back to the angel before patting the space beside him. The subtle gesture coaxed Cas into action. He stood up and stripped down to his baby-blue boxers – which happened to be Dean's favorite thing to watch – before crawling into bed next to his husband. Dean's arm automatically hooked around Cas's torso, like it did every night, and he pulled the angel close with a smirk. Cas, however, seemed to be lingering in his own thoughts.

“I... I still don't think it was wise for us to allow Jude and Clarence to share a room tonight, Dean,” he mentioned, voice low and honest.

“Hmm,” Dean smiled, amused by how protective Cas still was of their son, “It'll be okay, Cas.”

A moment of silence ticked by, in which Dean snuggled close to his angel and felt sleep threatening to take over, before Cas spoke again.

“The thought of them kissing each other before bed causes me great discomfort,” he murmured.

Dean's eyebrows furrowed. Kissing? Wait, did Cas seriously think that Jude and Clare were only going to make-out tonight? Dean lifted his head to properly look at Cas's face, seeing the somberness and innocence in his eyes. Oh, God. It was true. Cas had no idea that those boys were probably banging each other senseless right about now... The angel blinked back at the hunter in confusion.

“What?” he asked.

“N – nothing, babe,” Dean grinned, laying his head closer to Cas's shoulder so that he could peck it with his lips, “Just try to relax. I'm sure they won't kiss for long.”

Cas exhaled and readjusted himself, leaning close to kiss Dean's forehead before rolling back to stare up at the ceiling.

“Very well. Goodnight, Dean,” he said lowly.

Dean savored the feeling that Cas's rumbling deep voice gave him, smiling against his pillow as he closed his eyes.

“Night, Cas,” he whispered, feeling like the luckiest guy in the world.

 

**Notes for the Chapter:**

> Poor Castiel. He just can't imagine his baby boy doing adult things, can he? Thank goodness Jude's room is so far away from his parents'. XD You guys, I was SO excited to hear from all of you! Chuck knows how much I've needed to hear your words this summer! :) And I hope you are liking the story so far. As you can probably tell, Clare is still having a few issues in the bedroom, but Jude is helping him work through it. (Though he didn't mention it in this chapter, I think another reason Clare didn't want to top Jude was because he's always viewed the 'top' guy as the one that gets all the pleasure, and he always wants Jude to have all the pleasure. I hope that makes sense. Lol) :) By the way, that line Jude says - “You could never hurt me” - actually came from Avengers: Infinity War. When Vision said that line to Wanda I totally bawled my eyes out, so yeah. I knew I had to include it in this story. Lol. :D I know that Crowley's decision to keep the 'father' business away from Clarence seems bad, but he has good intentions. More about that will come soon. ;) I hope that you are enjoying the pace of this story. I know that Jess and Ollie haven't been in it very much yet, but they will have some of the spotlight in the next chapter. It will be out soon! Thank you so much for reading! :D


	3. Chapter 3

The morning after Clarence proposed to Jude, Jessica woke up feeling lonelier than she ever had before. Her big room felt so empty and quiet; so strange and foreign that she didn't even feel comfortable in her own bed. She tossed and turned for several minutes, hoping to find some relief so that she could get a little more sleep. But it was useless. Jessica didn't need sleep. What she really needed was Ollie...

With a gruff sigh, Jess eventually sat up and tossed her legs over the side of the bed to stare down at the fuzzy rainbow rug under her bare feet. She was really happy for her cousin and his boyfriend – now fiance. But if she was being honest, part of her was kind of jealous. Jessica was sure that she should have been engaged to Oliver by now. While she had never seen the proposal in any of her dreams, Jess knew that Ollie was going to marry her and start a family. In fact, she had seen herself married and pregnant by the time Jude and Clare's wedding rolled around – so what was the hold up? Was Ollie too scared or nervous to ask her? … Or were her visions wrong? What if all the things she saw were just dreams instead of premonitions?

A tiny bark startled Jessica out of her thoughts.

Jess flinched at the sound and looked down to see Papa's dog smiling up at her. Dickie was now sitting in between her feet on the rainbow rug, with his head tilted and tail wagging. Seeing him brought Jessica a little reassurance – and gave her an idea. It was Saturday morning, which meant that Ollie was currently working at the animal shelter in Lebanon. Right about now, he was probably waist deep in walking dogs and feeding cats. Maybe he wouldn't mind an unannounced visit from his girlfriend.

“Hey, Dickie,” she smiled, reaching down to run her fingers over his head, “I'm gonna go see Ollie. Wanna come?”

Of course, Dickie barked excitedly and ran around the room like a rabid pup. He was always excited to visit the animal shelter, for obvious reasons. The dog's playful acrobatics made Jess giggle as she walked around to get dressed. Poor Ollie was probably working really hard this morning, so she wanted to give him a good distraction by wearing a nice outfit. She chose a golden sundress with a rosy floral print that Ms. Jane bought her, a pair of brown knee-high 'ass-kicking' boots that came from Aunt Rowena, and some rabbit-themed jewelry that she got from her parents. Jess even took the time to curl her long blonde hair and spritz herself with some pheromone-infused perfume for good measure. She wanted to look absolutely perfect for the love of her life today. By the time Jess finished dolling herself up, Dickie was laying on the floor and yawning.

“Yeah, I know. Sorry it took so long,” she muttered to the dog, holding her arms out, “C'mon, boy. Let's go.”

Dickie sprang back to life at once, hopping up to catapult himself into her arms. With the dog secure, Jessica flew herself away from her bedroom in the bunker, and landed in the animal shelter all the way across town within the blink of an eye. She made sure to pop into one of the supply closets in the back, just in case there were other people around. The closet was full of pet food, medicine, brooms, mops, cages, and other supplies, but void of humans. Jessica sat Dickie on the floor and straightened out her clothes before slipping over to steal a peak out the door

As usual, the animal shelter was loud; full of barking dogs and meowing cats. By the tone of their excitement, it was morning feeding time, which meant that Ollie was handing out food. Jessica's assumption was proven right when she spotted his red hair bobbing along the top row of cages across the hall. The voice of his boss echoed from the back of the building as Jessica and Dickie ventured out of the closet.

“ - and don't forget the hounds outside, alright, Red? Last time, ya forgot,” the old man called.

“Don't worry, Mr. Harold. I've got it,” Ollie replied, his voice bland and weak.

Jessica hated hearing that Ollie was so unhappy, but she knew she was about to make his day a thousand times better. Wanting to catch him off guard, Jess tip-toed down the corridor to the end of the line of cages and waited for him to approach from the other side. As soon as Ollie was close enough, she stepped around and smiled.

“Hey there, handsome!” Jess smiled boldly.

Oliver nearly jumped out of his skin. He gasped and jerked his hand up, which accidentally caused him to spill dog food everywhere. Jessie giggled and covered her mouth. Oh no! She didn't mean to scare him that badly!

“J – Jess!” Ollie said, though he wasn't smiling as much as she hoped, “What are you doing here?”

“I came to see you, silly,” she pointed out, “Sorry about that. Here, let me help.”

With the snap of her fingers, Jess used some grace to clean up the spilled dog food. It all swirled up from the floor and twisted its way back into the bag, much to Dickie's disappointment. Ollie watched it happen, but he still wasn't smiling. It wasn't until Jessie studied his face that she noticed the dark circles under his eyes and the paleness of his already-pale skin. Ollie looked like an exhausted ghost under his many freckles. Was he not getting any sleep?

“Ollie, you look exhausted,” Jess pointed out in a serious tone, reaching out to take his face in her hands.

“That's because I am,” he admitted, allowing her fingers to rub his cheeks, “I was up all night studying for that stupid biology midterm, which made me late getting up for work this morning. And my dad's wanting me to meet him at the batting cages in an hour to practice, but I have to finish up here and swing by the house to pick up my gear before I -”

Jessica silenced Ollie's anxious rant by leaning forward to press her lips to his rambling mouth. She hoped that a soft, gentle kiss would calm him down and make him feel better. After all, his kisses always did the same for her. Their tongues gently rubbed together for a moment while the barking dogs serenaded them – until Ollie's boss called from the back again.

“Red? You finished with that yet?”

Ollie carefully plucked his lips away from Jess's and backed up to heave a forlorn sigh.

“Working on it,” he called back before lowering his voice, “I'm sorry, Jess. I really don't have time to talk right now.”

“That's okay. I'll just talk to you,” she said, backing up so that Ollie could keep working, “So, um, I don't know if you heard about it yet, but Clare proposed to Jude last night.”

Ollie stopped in mid-scoop and his brown eyes flew wide. He glanced at Jessica in shock before giving the next dog some food.

“H – He proposed?” Ollie muttered, unaware that he was missing the dog bowl as he poured it, “Like... like a 'marriage' proposal?”

“Yep,” Jessica nodded, casually turning around to admire the animals behind her and pet one of the stray kitty cats, “Oh, I wish you could have been there. It was _sooo_ sweet. Clare just went on and on about how much he loves Jude and how he never wanted to be without him... It was so romantic.”

Jessica was using the most alluring voice she could muster, trying to lay on the heaviest hint possible. She was hoping that hearing about Jude and Clare's proposal might inspire Ollie to give one to her. But Ollie seemed almost too shocked – or distracted – to catch onto the subtle messages. Dickie danced around Ollie's feet as the guy finished one row and started on the next, greeting all the other animals with a sniff and a pleasant bark.

“Huh,” Ollie said, “I, uh... I never thought of Clarence as the romantic type. He's got more of a bad-boy complex, if you ask me...”

“Well, he did a great job. Even played his guitar and set up the bunker with candles. It was beautiful,” Jessie went on, swishing her dress around and batting her eyelashes, “Jude is so lucky. Maybe one day, something like that will happen to _me_...”

Jessica wasn't even being subtle anymore. She was practically asking Ollie to propose to her. But whether it was from exhaustion or stress, Ollie didn't seem to notice. He just fed all the hungry animals, keeping his sight focused on his work.

“Yeah. Sounds great,” Ollie mumbled, clearly not paying attention to Jess's words.

Part of Jessica felt like rolling her eyes and throwing her hands in the air because Ollie was acting so aloof. But the other part of her felt kind of bad for him. He seemed to be going through a really rough time right now, between work, school, and trying to spend time with each of his parents. Ollie didn't need the added stress of proposals right now. He needed to take a breath.

“Hey,” Jess said.

She reached out to take his arm and pull him away from the dog cages again. Once he was in the middle of the hall, Jess wrapped both of her arms around him and held him as close and tenderly as possible, bringing her lips to his ear.

“Everything's going to be okay,” she promised.

All at once, the containers in Ollie's hands 'thumped' to the floor and his arms circled back around Jessica. His fingers slid up the back of her slinky dress and held on tight as he rested his head on her shoulder. Jess could almost feel the tension loosening from his muscles and his fast heart rate slowing. She was glad that her hug could help him feel better.

“I miss you all the time,” Ollie mumbled so faintly that Jess barely heard it.

Before Jess could explain to Ollie how much she missed him too, the old man's voice echoed from the back again. Jessica nearly groaned out loud when she heard it. Ugh. Why couldn't he leave Ollie alone for five minutes?!

“Red? You done with that yet or what, kid? I've gotta get to the post office by noon and I'd like to lock up,” he called.

Ollie lifted his groggy eyes and took a breath to reply, but Jess quickly covered his mouth with one hand. She used the other to snap her fingers again, using her grace to disperse the rest of the food to the other animals, including the ones outside the building. She also tidied up the cages, got rid of the waste, and cleaned up the floors. All with a single snap. The animals were all content afterward, happily eating their food, which quieted down the whole building. Ollie glanced around at the changes, his weary brown eyes growing large with surprise. When Jess finally removed her hand, he was able to call out.

“Y – Yeah. All done,” he loudly confirmed to his boss, before lowering his voice and smiling fondly at his girlfriend, “You are an _angel_.”

“I know,” Jess nodded with a wink.

Ollie finally smiled brightly for the first time since Jess got there – but it soon disappeared when his phone started to ring from his pocket. It was the Darth Vader theme song, the ringtone that was assigned to his dad's number. Ollie exhaled and shook his head as he dug out the phone and looked at the screen in despair. Jessica secretly hoped that he wouldn't answer, but Ollie swiped the answer button and held the phone to his ear anyway.

“Yeah, Dad?” he asked.

From the close proximity, Jess could hear Eddie Thompson slightly rising his voice to his son. The guy was explaining that he wouldn't be able to keep their spot at the batting cages for much longer and that Ollie needed to get over there as soon as possible, or else they wouldn't get to practice today. But from the look of total blandness on Ollie's face, it seemed like he didn't want to go at all. And even though he really needed a nap instead of more physical activity, Ollie still obliged his father.

“Okay. I'm leaving work and I'll be there in less than twenty minutes,” he promised, voice frail and emotionless.

Eddie Thompson barked some kind of reply before hanging up, which left Ollie without so much as a goodbye. He lowered his phone and blinked at it wearily before stuffing it back in his pocket and returning his attention to Jessica.

“Jess, I – I'm really sorry, I know you came all this way to see me, but I've gotta go,” he admitted, his tone much more disappointed and sad than when he was talking to his father.

Though it kind of broke Jess's heart, she nodded and clung to the smile on her face, not wanting Ollie to be anymore upset than he already was.

“It's okay,” she breathed, “Maybe later, we can -”

“Red,” Ollie's boss interrupted again, “Tick-tock, boy! The post office is a callin'!”

Jessica clenched her jaw and momentarily glared at the ceiling. She had half a mind to snap her fingers again and paste that old man's mouth shut, but she resisted the urge. Ollie seemed just as upset as she was about having to be apart. His cocoa eyes circled her whole face a few times before he leaned in to kiss her properly. Jessica's own eyes fluttered shut to enjoy the sensation, not knowing the next time she would get to taste her love's kiss. Ollie's arms squeezed her tight too, pressing their fronts together warmly. He pulled back and let go of her completely after a few seconds, slipping away like a faint memory.

“I wish I could stay with you, but I can't right now,” he admitted, already walking around her, “I love you, Jess. I'll text when I can. Say hi to the guys for me.”

“I – I love you too!” Jess called urgently.

Ollie tossed a hand up to signal that he heard her, but he didn't slow down. He was out the door before Jessica could even think of anything else to say, leaving her standing in her nice dress among all the caged animals. Somehow, Jessica could feel the same emotion she woke up with starting to crawl back into her chest. She was all alone again, missing Ollie like crazy, wishing that her future dreams would hurry up and come true...

A tiny 'pat-pat' on her boot made Jess look down. Dickie was pawing at her from the floor, looking up with sweet puppy-dog eyes. It was almost like he knew that she felt bad and wanted to comfort her. Jess sighed and picked up her Papa's dog to hold him in her arms again.

“I guess it's time to go back home,” she mumbled.

After taking a final glance at all the other animals, Jess flew back to her bedroom in the bunker. Her room was just the way she left it. The air even smelled like the perfume she used just minutes before. It kind of bummed her out to think she didn't even get to see Ollie that long, but maybe it helped him. Dickie licked Jess's cheek a few times, probably to cheer her up, before she sat him down on the floor again.

“I'm okay,” she assured, even though she wasn't, “Let's go find Dad and Pop.”

Still wearing her nice outfit, Jess breezed out of her bedroom to greet the rest of the bunker. Across the hall, Jude's bedroom door was still closed, so she assumed that he and Clare were still sleeping – or doing other things. So she wandered on down the hall to the kitchen, where everyone else was congregated. Dean and Cas were sitting at the table with uncle Bobby, Crowley, and Aunt Rowena, chatting about some new case. But Jess's parents were hovering near the coffee maker beside the counter, and Dad was holding his head in both hands.

“Gabe. I'm never drinking with you again,” he growled to Papa, “Ugh, my head feels like a sack full of rocks and sandpaper.”

“Awww, does my sweet lil diva-moose have a hangover?” Papa cooed, “Here, lemme see that head of yours.”

Dad grumbled but leaned over to let Papa patch him up. It only took a little touch of Pop's grace to heal Dad up. His pale face refilled with color, the red disappeared from his eyes, and he took a large refreshing breath.

“There. Now you're ready to join the next Miss America Pageant,” Papa winked, his golden eyes flickering to Jess and growing wide, “Jessie-Rabbit! Good morning, baby girl! Whoa, you look so nice! What's the occasion?”

Papa's loud praise claimed everyone else's attention and they all turned to look at Jessica. Her uncles and aunt smiled brightly, eying her dressy attire and beaming.

“Look at you, Shortcake. Got a hot date today?” uncle Dean asked.

Jess only shook her head. Nope. No Date. Not today...

“Dean Winchester, ya stop that prissy ramblin' right now,” Aunt Rowena hissed, “Unlike you, our lovely lass doesn't need a special occasion to dress nicely. Isn't that right, love?”

Jessica smiled back at Rowena, feeling her earlier disappointment slipping away. She loved having Aunt Rowena around. Sometimes, it felt like Aunt Rowena was the only one who understood how she was feeling. Maybe it was a girl thing.

“Ya know what?” Rowena continued, turning in her seat to fully appraise Jess from head to toe, “I think our lady-rabbit should join me in the lounge tonight.”

Dad, uncle Dean, and uncle Bobby all nearly spit out their coffee at the same time. And uncle Crowley nearly jumped from his seat.

“Absolutely _not_!” he growled.

Jess glanced around the room, feeling so confused. What the heck was everyone so upset about?

“The lounge? What lounge?” Jess asked.

“Well, sweet cherub,” Aunt Rowena continued, “the lads here are tryin' to catch a magic man who's been feedin' off Fergie's livestock -”

“ _Demons_ ,” uncle Crowley huffed, “He's killing _demons_ , you half-wit wench!”

“ - and they've recruited me to stand in as 'bait' while they all converge to take him down,” Rowena explained, ignoring the interruptions to smile at Jess, “Because of me ravishing looks, 'o course. And since yer already dolled up, I don't see the harm in ya taggin' along to the lounge, where we're plannin' to catch 'em.”

“The harm, _mother_ , is that she might get caught in the crossfire!” Crowley spat accusingly.

“Uh, yeah, I'm with Crowley. This guy sounds like a real piece of work and Jess shouldn't be anywhere near him,” uncle Dean added.

“Agreed!” Dad announced.

Jessica's mouth fell open and she glared at all the men in the kitchen. How _dare_ they speak for her! Jessica was an adult now! She didn't have to take orders from them anymore! She was old enough and mature enough to make her own decisions! Luckily, Aunt Rowena seemed to be thinking the exact same thing, because she stood up from the table and crossed her arms.

“ _Shame_ on the lot of you. Ya haven't even given the poor lass a chance to speak!” Rowena barked before stepping over to give Jess a half-hug, “Don't let these boys scare ya, love. If you want to come with me, I'll take good care of ya. What d'ya say, dear? The choice is yours.”

Jessica looked around at her family, seeing apprehension in almost every eye looking back at her. All the guys were really worried about her being 'bait', but Aunt Rowena was right. The choice was hers. And if she wanted to help take down a demon killer, she had every right to do so. Jessica was through waiting for her turn to speak. Her turn to act. Her turn to be useful. This time, she was taking matters into her own hands.

“That magic man is as good as caught,” Jess predicted.

* * *

The lounge in which the Winchesters staged the ambush of their newest monster was located in St. Louis, Missouri. Jessica had never been there before, but with the help of her Papa and uncle Cas, she was able to fly to the lounge along with everyone else. Jude and Clare were the only ones that stayed behind at the bunker. Uncle Crowley explained that he didn't want them to come because they were 'celebrating their engagement' and he didn't want to disturb them. But Jess could tell that there was another reason he didn't invite them, though she couldn't tell what it was.

Uncle Bobby explained that the best way to catch a wizard was to ambush him, pin him down, and knock him out as quickly as possible. If left awake, he would be able to say spells and cast magic that would help him escape, so knocking him out was a must. The plan was that Aunt Rowena – and now Jessica – would sit at the bar and lure him in to talk, while all of the Winchesters converged on him to take him out. It was well thought out too, because each man would be stationed near an exit point, preventing their target from fleeing. Jess commended her fathers and uncles for their clever idea – and constantly reassured them that she would be fine – before following her Aunt Rowena to the center of the room.

Jess had never been in a lounge before, so she had no idea what to expect. It seemed like a fancy establishment. Lots of well-dressed people chatting and sipping on alcoholic drinks while listening to low jazz music. It had a calm and sophisticated atmosphere that Jessica had a hard time getting used to. It was so classy; almost arrogant. How was she supposed to blend into the scene of a place like this? Aunt Rowena, on the other hand, seemed right at home. She smiled and waved to other patrons as if she had known them her whole life, sashayed to the bar in her fancy red dress, and ordered a drink without so much as batting an eye. Jessica really admired her aunt's ability to act so mature and collected. She wished she could be as confident and motivated as Rowena.

“How do you do that, Aunt Rowena?” Jess asked quietly once they were seated, “I mean, you're so confident. I wish I could be like that...”

“Confidence is an acquired skill, my love, much like playin' the piano,” Aunt Rowena purred, “The more ya practice, the better you'll be at it.”

Jessica smiled and gently swiveled around on her bar stool. She loved getting advice from older females, especially the ones so close to her heart... Jess fiddled with a napkin on the counter and smiled at the bar tender before asking her aunt a question that had been bugging her.

“So, how are we supposed to lure this guy in again?” she asked.

Rowena sipped her drink and winked at a random guy before answering.

“Fergus told me this fellow enjoys the company of demons,” she admitted, “So, to entice the lad, I took a potion of me own making. For a short time, it gives me a powerful demonic aura. I reckon it'll be like a black beacon that the magic man can't ignore. And once he gets a good oogle at me wears,” she said, pausing to adjust her low-cut dress, “He'll be so distracted that he won't notice our boys comin' in to get 'em.”

Jessica nodded and turned to hide her smile. Oh, Aunt Rowena. She was so willing to offer her 'wears' to anyone that would give her a good look... Several minutes ticked by, in which the two ladies just sat there and looked around. Jess glanced at the stranger's faces, secretly searching for one that might seem out of the ordinary. Every so often, she caught a glimpse of her parents or uncles wandering around the establishment, also looking for someone suspicious. But a few minutes turned into an hour, and there still didn't seem to be anyone interested in Aunt Rowena's aura.

' _This doesn't seem to be working_ ,' uncle Cas said over the angel radio, which sounded off in Jess's mind, ' _Either Crowley is mistaken or our target has already left the premises_.'

' _Eh, just keep an eye out Cassie. It's not like you've got anything better to do right now_ ,' Jess's Papa replied.

' _That is not true, Gabriel_ ,' Cas argued, “ _There are plenty of other things that I would rather be doing right now, including D -_ '

' _I see him,_ ' Crowley's voice interrupted.

Jessica gulped and sat up straight on the bar stool. She felt the urge to whip around and search for the person Crowley was talking about, but she didn't want to give herself away either. She tried her best to remain calm and listen to her uncle Crowley's prayers.

' _He's approaching the girls from the western entrance_ ,' the demon continued, directing his voice to Jess, ' _Jessica, let mother do all the talking. The rest of us will slowly converge._ '

Though she felt the desperate need to turn around and look for the man, Jess kept facing the bar. It was only a few seconds later that she felt someone approach behind her. The hairs on the back of her neck stood on end and she could feel goosebumps on her skin. Whoever was there was oozing evil...

“Mighty clever, isn't it? A Scot drinking scotch..."

The man's voice was deep and accented, though Jessica couldn't tell which country it was from. He was obviously talking to Rowena and Jess was glad. Because, at the moment, she couldn't find the nerve to turn around. Beside her, Rowena gave a giggle.

“Well, ya know what they say,” she purred, “A fiery lass needs a fiery dri -”

When Rowena's sentence stopped abruptly, Jessica's worry outweighed her fear. She finally turned to see why her aunt had stopped short, and found the red haired witch gazing into the eyes of the stranger. Only, she wasn't smiling anymore. And neither was he. They were both staring at each other without blinking, mouths open, and faces frozen in shock. Obviously, they knew each other. But their interaction didn't worry Jessica as much as the appearance of the stranger did. His hair was dirty blonde, like straw, and his eyes were a vibrant brown, almost scarlet. He seemed older than Jess, closer to her father's age than hers, but his presence felt _much_ older than that. The most defining feature of his face was the faint scar etched from his right cheekbone all the way down his neck. This 'magic man' seemed handsome on the surface, but he was haunting. Vicious. Detestable. _Evil_...

“... C... Caldwell...” Rowena breathed, her voice hollow as she clutched her own throat in horror.

“Rowena,” he replied, his eyes narrowing, “What are you -?”

' _Now!_ ' uncle Crowley shouted over the radio.

Jessica wasn't sure what came over her. The urge to help mixed with the panic and fear of being close to someone so evil made her snap into action. And before any of the other Winchesters even started toward the bar, Jessica reached out to grab the man by the arm. She used her grace to clamp him in a tight hold, which made golden light shine from her skin. The man looked down at her hand before meeting her eyes in surprise.

“You're not going anywhere,” Jessica barked.

Bold hostility flashed in the man's reddish brown eyes. He lifted his free hand, which also lifted the shelf behind the bar. Jessica barely had time to turn her head and look at the floating shelf before it came flying right at her, smacking her in the shoulder so hard that she fell off the bar stool – and let go of his arm. Once he was free, the man bolted for an exit, shoving his way through the crowd. Dad and Papa both rushed to her side to see if she was okay, but Jessica's mind was far from her own well being. She was _not_ about to let that evil man leave. Especially after he threw a shelf at her!

Jessica flew from the floor and popped up in front of the running man. She tried her best to grab him again, by he pushed her away with an unseen force. Jessica bumped up against the wall behind her, but quickly chased after him. He sprinted his way toward a side door and shoved his way outside – where uncle Crowley was waiting in the alley with a knife in hand. The man stumbled outside and stopped short, meeting Crowley's eyes with a fighting stance. And while Jessica was happy to see her uncle blocking the man's way, the look of absolute horror on Crowley's face made her stomach turn. Oh, no, did Crowley know this man, too? How?!

“No,” Crowley said, slowly shaking his head, “Not you... No! I _killed_ you!”

“That you did,” the man agreed, “but it wasn't the first time I've died. And it certainly won't be the last.”

The man's bizarre statement only outraged uncle Crowley. He yelled in anger as he lunged forward with the knife. The magic man missed the weapon, swooping from side to side to avoid the sharp edge. Jessica tried to catch an opportunity to jump in and help Crowley, but the two of them were fighting in such a blur that she didn't know where to start. At one point, the man whispered something and flicked his hand, which magically ripped the lid off a nearby dumpster. The metal panel flew across the alley toward uncle Crowley but he dodged out of its path.

Unfortunately, when Crowley avoided the dumpster lid, he jumped right onto the end of the _magic man_ 's knife...

Jessica didn't even realize that he had a weapon until it was already buried in Crowley's stomach. The demon groaned and clutched at his suit jacket where the knife was stuck in him, dropping the one in his own hand. Jessica gasped and covered her mouth. No! Uncle Crowley was stabbed! Using the knife, the magic man pulled the demon close to his face to speak.

“I let you win last time,” he hissed, shaking his head of blonde hair, “But my generosity has worn thin. Much like my tolerance for your _weaselly tricks_ ,” he suddenly yelled, voice echoing and making Jess flinch, “Before you die, demon, make yourself useful and tell those bastards to leave me be, lest they meet the same fate.”

After his angered demand, the man removed his knife from Crowley's stomach and tossed him on the ground, causing uncle Crowley to groan out in pain. Jessica immediately ran to kneel down next to him, to shield him just in case the magic man tried to hurt him anymore. But the guy had already backed up and retrieved something from his pocket. It was a small pouch of black dust, which he threw on the ground and his feet. And when the smoke dispersed, he was completely gone...

Although Jess was worried that the bad guy got away, she was more concerned about uncle Crowley. He was gritting his teeth and breathing harshly, holding the stab wound in his stomach.

“It's okay, Crowley, I can heal you,” Jess promised.

She frantically reached out to cover the wound and let her grace shine from her shaky hand – but it wasn't working. Her grace wasn't healing him like it was supposed to. Jessica gasped and tried harder, exuding as much power and heavenly energy as she could, but it wouldn't heal. Something was preventing her grace from working on him.

“D... demonic black magic,” Crowley wheezed, pushing Jess's hand away, “Only mother can help me now...”

Before Jess could question what he meant, the stampede of their family's footsteps came rushing from the building. The rest of the Winchesters swarmed around Jessica and Crowley instantly, searching for the bad guy but making sure they were okay.

“Oh God, what happened?!” Jess's Dad blurted.

“Where did he go?” uncle Cas barked.

“Crowley, are you alright?” uncle Dean knelt down to ask.

“No,” Crowley groaned, rolling his head back and forth, “No, you... you were right, Dean... It... It's him...”

Jessica looked up to her uncle Dean and could see the surprise and disappointment on his face. What where they talking about? Who was the guy that hurt uncle Crowley?!

“Who?!” Jess nearly shouted.

“Dean, what's going on?” Dad asked, sounding just as lost.

Uncle Dean took a second to glance at all the people around him, even Rowena, who had followed everyone outside. He momentarily shared a defeated look with Crowley before lowering his head.

“The bastard is Clarence's father,” he admitted.

 

**Notes for the Chapter:**

> Dun. Dun. DUUUH!!!! XD Yep. That Bastard is Clare's father. But you probably saw that coming though, huh? Lol. ;D “But how can that be?” I hear you asking, “Crowley killed him in the desert! How is he still alive?! And how does Rowena know him?!” Not to worry, my beautiful ducklings! All your questions will be answered soon enough! ;) But I will go ahead and ruin one theory for you: Caldwell is _not_ Crowley's father. I repeat: Clare's father and Crowley are _not_ related. (Sorry if that burst some bubbles, but it had to be clarified. Lol) I actually feel really bad for making Ollie so stressed out. That poor kid is being pulled in all directions. And not in the fun way :( But things will change for him as the story goes on too. ;) I know this chapter probably left you with a lot more questions than answers, but we will be discovering all the facts together! I promise! ;) Thank you guys so much for reading and reviewing! The next chapter, which will give you some of those answers, will be out soon! :)


	4. Chapter 4

“Mmm, it smells amazing in here,” Clarence purred behind Jude, “Whatcha cookin', good lookin'?”

A smile spread across Jude's face as he stirred the boiling pot of noodles in front of him. The smell Clarence was talking about was the heavy and pungent aroma of the garlic bread baking in the oven. And maybe some of the tomato and basil scented sauce simmering in the smaller pot nearby.

“Spaghetti,” Jude answered without turning around.

“Spaghetti? Oh man, I love Italian,” Clarence replied, his voice getting closer and closer to Jude's ears as he walked up, “Especially with _meatballs_.”

As the last word hissed from Clare's lips, Jude felt a hand reach around to take hold of his crotch. Jude giggled and leaned away from the stove, bending himself further against his fiance to get away from his groping hand. Clare chuckled as they playfully wrestled each other in the bunker kitchen for a moment, only accompanied by Dickie's barks. The dog must have thought that the two of them were hurting each other, but they were only playing around. Jude eventually turned around to wrap his arms around Clare's shoulders and smile up at him.

The two of them – three, with Dickie – were all alone in the bunker today. Everyone else was off working a case, and Jude and Clarence were taking advantage of their time alone together. By walking around in nothing but their boxers and doing what ever they wanted. Jude thought it was weird for them to have such a huge, empty bunker all to themselves. But it was pretty fun...

“I didn't make any meatballs. But there are plenty of limp noodles,” Jude pointed out in the most serious tone possible.

Clarence's hardy laugh made Jude's smile return at full power.

“I guess I'll take whatever I can get, then,” the demon grinned, “Can I at least kiss the cook?”

“I would be offended if you didn't,” Jude nodded.

Clare smirked, staring down into Jude's eyes for a moment before craning his neck down for a kiss. Jude stretched up to receive it – but a loud bang made them both flinch back. It came from some other room in the bunker and instantly put Jude and Clare on guard. The demon turned around to face the kitchen door along with Jude, where they both waited and listened.

“What the hell was that?” Clare asked lowly.

A few more noises echoed to them, which almost sounded like books falling, before they heard a voice. It came from down the hall, in the direction of all the bedrooms.

“ _Jude? Jude?_ ” Papa's voice echoed in the distance as if he was searching for him.

Clare and Jude both exhaled with relief. Oh, it was only Jude's parents, back from their adventure with uncle Crowley.

“We're in here, Pop,” Jude answered.

Having heard Jude's voice like a prayer, Papa instantly flew into the kitchen. He appeared by the metal island in the middle of the room – and the moment Jude looked at him, he could tell that Papa was extremely unnerved. His eyes were large, he was spinning around urgently, and when he spotted the two boys, he dashed over to grab their shoulders.

“Come. Now. We must go,” he breathed in a panicked tone.

“What? Go where? What's going on?” Clare asked.

“Crowley has been severely injured,” Papa informed, “Gabriel has transported him to Bobby's house, where Rowena can best treat him. Quickly, we must get there and help in anyway we can -”

“Cas, this is everything we've got. Let's go,” Dad interrupted.

Jude, Clare, and Papa all turned toward the kitchen door, where Dad had walked up with a giant stack of books in his arms. It seemed as though he had ransacked the library for specific volumes of lore. The intensely worried look on his face made Jude feel even worse. Oh, no. Uncle Crowley must have been hurt really badly. He wasn't going to die... was he? Clarence turned to give Jude a very fearful and anxious set of greenish-brown eyes, as if he was thinking the same thing.

“Jude, please. We must go,” Papa urged, reaching his hand out.

Before Jude took his Papa's hand, he spun around to shut off the stove. He didn't want the bunker to catch on fire while they were gone. With the kitchen safe – and even though he and Clare were still only in their boxer shorts – Jude took hold of both his Papa's and fiance's hand. Papa grabbed Dad with his free hand and the four of them flew out of the bunker together. Jude squinted his eyes shut and braced himself, hating the violent inertia of being pulled through space. But when his feet landed on a solid wood, the sounds of frantic voices distracted him from the discomfort.

Jude opened his eyes to see the inside of his uncle Bobby's kitchen and study, only it wasn't the calm and peaceful atmosphere that it usually was. Their entire family seemed to be packed into the small space. Crowley himself was sprawled out on the coffee table. The top part of his suit was removed, revealing his bare, plump torso – and the oozing black wound on his stomach. The demon was thrashing around and groaning in agony, clutching the area as if it was causing him acute pain. From the few glimpses that he could catch between the people running around, Jude saw that the black wound had begun to spread; etching dark veins across most of his stomach. Jude didn't know whether it was from the pain of the wound or his outrage at being victimized, but something was causing Crowley's eyes to stay jet black. His demonic aura was on full display through his vessel. Even his voice was in an eery pitch when he cried out.

Uncle Bobby and uncle Sam were trying their best to wrangle Crowley as he rolled around. They were shouting over his groans, asking him to hold still and calm down, but it wasn't helping. To add more confusion to the chaos, Bobby's three hellhound dogs were whimpering and barking, bewildered and frightened by the commotion. In the meantime, uncle Gabe and Jessie were trying to clean Crowley's wound; dodging his flailing arms in order to pat the area with warm water. Jude thought that was strange. Why weren't they healing him with their grace? They could take care of it in no time flat! Why were they just washing it off?

As soon as Jude, his parents, and Clare popped into the scene, Aunt Rowena dashed straight over to them. Jude immediately realized that she had been crying, because some of her mascara had run down her cheeks. She reached out to clutch Clarence first.

“Clare! My d – darling boy!” she whimpered, patting his cheek, “I need ya to go to the garden and pick all of those rows of Kingsfoil we planted. Gather _all_ of it. Then, go and fetch me mortar and pestle from the basement. The golden set with the engravings on it. Hurry, lad. Go.”

Though he was completely lost and worried, Clarence nodded, gave Jude's hand one tight squeeze, and turned to run through the kitchen and out the back door. Before he was even gone, Rowena turned her attention to Jude's parents.

“Did you find them?” she asked over the sounds of Crowley's groans.

Dad sat all the books down on the table and began to sort through them.

“I brought everything we had on magical beings,” he explained, holding up a leather bound book, “including Dad's journal.”

“Yer father's diary?! Those scraps of ol' newspaper won't do Fergus any good!” Rowena snapped, ripping the book from Dad's hand and slamming it on the table, “We aren't dealin' with just any magical being, Dean Winchester. The man is a _Warlock_.”

A particularly loud cry came from the living room and momentarily distracted everyone. Crowley had fought his way out of Sam and Bobby's grasp and was now curled on his side, heaving low gurgles. Rowena gasped and ran to the coffee table, where she placed both of her small hands over his wound and began to chant a low mantra. Crowley's gurgling stopped, but his resistant efforts returned. He flailed again and muttered profanities, accidentally knocking Rowena's hands away.

“Rowena, do you know the man who did this?” Jude's Papa openly asked, “Your sudden surprise and hesitant actions at the lounge suggest -”

“Yes, alright?!” Rowena squeaked, a few tears escaping the corner of her eyes as she stared at her injured son, “H – his name is Caldwell. He's from Europe, same as me. I know him because... because _I'm_ the one who taught him the dark craft. He was a clever boy. Picked things right up. I was... sweet on him. For a long time... But when he told me he was goin' off to destroy Hell, I told him he was a bloody mad man. In all that time we spent together, I never realized that he was slowly morphing into a nutter.”

“Yeah, well, now he's a nutter _and_ a powerful wizard,” uncle Gabe grumbled.

“Not a wizard. A _warlock_ ,” Rowena corrected again, “There's a difference, lads. Wizards learn magic. Warlocks are blessed with magic from a higher being.”

“But you just said you taught him,” uncle Sam pointed out.

“Aye,” Rowena nodded, “I taught him the basics. But what he did tonight? That wasn't from me... After what he just did, it's clear that he's made a deal with someone very dark. And very strong...”

Another one of Crowley's groans interrupted the conversation. It made Rowena flinch and caused a twinge of sadness to appear on uncle Bobby's face. While he held on tight to Crowley's arm, Bobby flashed a pair of glistening eyes up from under the crooked bill of his hat.

“The man's in _pain_! Do somethin'! _Please_!” Bobby begged, his voice cracking a little, “Why can't ya just _heal him_?!”

“Because he was pierced with a cursed blade, Robert,” Rowena informed, “It's demonic black magic. It won't stop spreading until the curse is broken or – or it kills him. The only thing I can do is slow it down.”

“Well, how do we break the curse?” Sam asked.

“The only one who can break it is the person who made it,” Rowena admitted with a woeful sob.

“So, we're gonna have to catch the bastard and make him break it,” Dad concluded wearily, “Sammy, come and help me search these books. We've gotta figure out a way to catch this asshole.”

Jude turned away from the situation in the study to face the one in the kitchen. The table was cluttered with books, which Jessica and Dad were already looking through. Uncle Sam joined in and Jude felt like he should contribute too. He really wanted to go and help Clare outside, but there were so many books to look through and it seemed like uncle Crowley didn't have a lot of time. Jude reached out to pick up the nearest book to him, but Jessie caught him by the arm.

“Jude,” she whispered, “I need to talk to you.”

Before Jude could even ask what it was about, Jessie pulled him all the way to the other side of Bobby's kitchen. Once they were out of hearing range near the back door, Jess held up the book in her hand – which Jude recognized as their grandpa John's journal.

“So, this is going to sound really weird,” she began, keeping her voice low, “but, um, I think you should know that... The man who stabbed Crowley... Well, uncle Dean said he was Clare's dad...”

Jude felt like the wind had been knocked out of him. What? Clare's dad? His real father? But, it couldn't be Clare's dad. He was killed by uncle Crowley a long time ago. There was no way it could be him! Jessica must have seen the denial on Jude's face because she nodded.

“Yeah. It's crazy. I don't know if it's true or not... but that guy _did_ look a lot like Clare,” she admitted, glancing away, “Anyway, uncle Dean said that we probably shouldn't tell Clare yet, because it might upset him and Rowena really needs his help to take care of uncle Crowley while we catch the guy. But I... I think I might have a plan on how to do it.”

Jude gulped. He was momentarily stunned by everything he was hearing and it took him a second to regain his barrings. How could he _not_ tell Clarence that the person responsible for hurting Crowley – and raping Clare's mother, getting her pregnant, causing her to abandon him and start the cascade of tragedies in his life – was alive and well? Clare was Jude's fiance! He couldn't lie to him! But after hearing that Jess had a plan, Jude tried to maintain his focus.

“O – okay,” he breathed.

“Listen, you know how Rowena said that guy was a warlock?” she asked, to which Jude nodded, “Well, I've read grandpa's journal a few times and -”

“A few times?” Jude interrupted, “When?!”

“When I turned eighteen. Your dad let me read it,” she admitted, flipping through the pages to get to a certain one, “Anyway, there's an entry in here about a warlock. Grandpa John said that he summoned one by mistake, back in 1988. He doesn't go into much detail about it in his journal though.”

“So, how does that help?” Jude pressed.

Jessica paused to gulp and turn the open journal toward him. She pointed out a specific hand-written passage near the bottom.

“The entry right after it is pretty... familiar,” she hinted.

Jude took the time to look down and read the words that floated across the page.

_Aug. 19 th, '88_

_Two hunters came to the motel room last night. Girl reminded me of Mary. Guy seemed a little backwards. Said they were tracking a warlock. I told them everything I could about the one I caught, but wasn't much. Hope they catch the son of a bitch they're after. Shit. I hope I catch the one I'm after, too... Not a day goes by that I don't miss Mary. Sammy still cries for her... It's almost nine A.M. Gotta get the kids up. Meeting Bobby later._

_\- JW_

Jude read the paragraph twice, hoping to see the hidden message that Jessie was pointing out. So, there were other hunters that were chasing warlocks? Maybe the Winchesters could get in touch with them now. Would those hunters still be around after nearly three decades?

“You think we can find those people that grandpa John talked to?” Jude guessed.

“N – no,” Jessie denied, scooting even closer to talk lower, “I think that those two people who visited him are... are _you and me_.”

Jude narrowed his eyes. What? Jessica thought that she and he visited grandpa John? Way back in 1988? But that wasn't even possible. Was she feeling okay?

“Jess. We cannot travel through time. It's impossible,” Jude said, stating every syllable carefully in case she was losing her sanity.

“Oh, come on, Jude. You of all people should know by now that nothing is impossible,” Jessie replied with a smirk, “We _can_ do it. Dad told me that angels can travel through time. Besides, I... I had a dream about meeting grandpa John in a motel room. I had it a long time ago, but I remember it... Please, Jude. We have to go and ask him about this warlock -”

“Jess,” Jude interrupted, feeling anxiety creep into his chest, “Even if angels can go back in time, we still don't know how to do it.”

“I was going to ask uncle Cas to take us,” she explained.

“What? Papa? Why?” Jude asked.

“Because Dad said that he sent him and uncle Dean back in time before. More than once, actually,” she nodded.

Jude exhaled a large breath and looked around the kitchen. The thought of traveling back in time made him extremely nervous. Partly because he didn't want to leave Clarence's side, and partly because the thought of flying that far scared him to death. What if it was worse than flying normally? What if something happened and they couldn't make it back their current time? What if grandpa John tried to kill them because he thought they were dangerous strangers or something? There were countless things that could go wrong if they tried to attempt this!

A fast, sudden breeze brushed passed Jude and he looked up to see the blur of his fiance running by him. Clare bolted into the study with armfuls of weeds and the mortar and pestle aunt Rowena requested. Seeing Clare's frantic determination to help Crowley seemed to spark some courage in Jude. As much as he disliked the thought of time travel, Jude had to admit that Jess was right. If they didn't find a way to catch the guy responsible for hurting Crowley, he was going to die. And their family – especially Bobby and Clarence – would be devastated. Jude shook his head but eventually raised it to look at his cousin.

“Papa's not gonna like this plan,” Jude predicted.

* * *

“I do not like this plan,” Papa stated boldly.

Jude turned to give his cousin a firm 'I-told-you-so' look. The three of them, Jude, Jess, and Jude's Papa, were standing outside Bobby's garage in the dark, whispering under the streetlight. Jude had put some clothes on – old ones from uncle Bobby's storage that Jessie said would 'blend in better with 80s attire' – and had just listened to Jessie explain her entire plan to his Papa. Only Jude's Papa didn't like it one bit.

“Uncle Cas, look at his journal,” Jess encouraged, holding out the page she showed Jude earlier, “See? It's proof that we've already done it!”

“John Winchester could be describing anyone with that paragraph,” Papa pointed out, “Besides, traveling back and forth through time can be a confusing affair. I have no way of knowing how John Winchester would react to meeting people that look so familiar to his own children. And even if I did take you to that time, I wouldn't even know where to locate him on -”

“He's in room 15, in a motel outside Memphis, Tennessee,” Jessica blurted, pointing to the journal page, “It says so right here. Please, uncle Cas, we need to speak to him. He's the only one of us who has actually caught a warlock before! Don't you want to help Crowley?”

“Of course I do,” Papa answered sincerely, though he shook his head, “but this... This is a very sudden and undeveloped plan. Perhaps we should ask Dean if -”

“We don't have time!” Jessica suddenly interrupted, grabbing his arm and putting on her best 'puppy-dog' look, “Cas, I know this is a strange and dangerous idea, but I... I _have_ to help Crowley. It's _my_ fault that he's hurt. I should have jumped in to fight that magic jerk when I had the chance, but I didn't. I just stood there and watched him stab Crowley,” she squeaked.

Papa opened his mouth to dispute Jess's self blame, but she spoke over him again.

“So, please,” she almost begged, taking Papa's hand, “Let me do this.”

Papa looked back and forth between Jessica and Jude for a moment, and Jude could tell that he was slowly giving in. Though he didn't like the idea of not consulting the rest of their family first, Pop could see that Jess was genuinely determined to talk to their grandpa. Eventually, Papa sighed and held his free hand out to Jude.

“Son. You will need to hold on to me. This will not be a pleasant flight for you,” he warned.

Jude gulped, but stepped up to wrap an arm around his Papa. He gripped Pop's trench coat with a firm grip as he felt Pop's arm bend around his shoulder. Jessie hid their grandpa's journal inside one of Papa's many coat pockets before she hugged him too. Once both young adults were attached to him, Papa's eyes lit up with grace and he inhaled a large breath before take off.

Traveling backward in time was a lot like flying. There was a bright flash of light, a sudden yank on Jude's grace, and a gut-churning sensation of being dropped from a great height. The event made Jude's skin crawl and caused him to cling to his Papa like he did when he was just a child. When he felt solid ground under his feet a few seconds later, Jude was relieved, but felt utterly sick to his stomach. He clung to his Papa for an extra few seconds, attempting to keep the vomit from rising in his throat.

“Jude? Are you alright?” Papa whispered against his ear, giving him a half hug.

“Y – yeah. I'm okay,” Jude lied, not wanting to upset his Papa any further.

When Jude finally opened his eyes and stepped back to look around, he saw that the three of them were now standing near a two lane road, next to a motel. All of the cars parked in front of the rooms were older models – or were they 'current' models? From the vintage design of the motel, to the lit phone booth planted nearby, Jude was starkly aware that he was standing in a different time. Papa had done it. He had brought Jude and Jessica back in time to 1988...

“I'm giving you fifteen minutes,” Papa said, gaining Jude and Jess's attention, “Do not tell him who you really are or mention any events that occur between this time and ours. In fact, you should tell him as little about yourselves as possible. Just find out as much as you can about the warlock and meet me here afterward.”

“Meet you? You're not going in with us?” Jude asked.

“No, son,” Papa denied, shaking his head, “It's better that I remain as far away from John Winchester as possible. For his own safety...”

Jude gulped, hearing the underlying anger in his Papa's tone. Whoa, Papa really didn't like Dad's dad...

“Okay. Come on, Jude. Let's go,” Jessica called.

Jude gave his Papa a last look of understanding and reassurance before following his cousin toward the motel rooms a few feet away. Jess made a path straight to room 15, but Jude found it difficult to keep his feet moving. His stomach was still gurgling from the recent flight _and_ from nervousness. He had never met his Dad's dad before. What if he was mean? What if he didn't like Jude? What if he found out that Jude and Jess were really his grandchildren from the future? Though he was tempted to get upset, Jude tried to focus and calm himself. ' _Do it for Crowley_ ,' Jude told himself, ' _Do it for Clare_.'

Jessie took a large breath before gently knocking on the door. Jude could feel his heart beating in his ears as they waited and listened to the heavy footsteps approaching from the other side. They slowed to a stop and there was a moment of silence before the door opened a little. It was still closed with the chain lock, but a man peeked through the gap to look at the two young Winchesters outside.

“What do you want?” he asked in a gruff tone.

Jude swallowed harshly, trying his best to see the shadowed face in the door. The man was tall, had a five o'clock shadow, and reeked of alcohol. But his demeanor was acute and harsh. If he had been drinking, he held his liquor pretty well. He didn't seem drunk at all. Only exhausted and very irritated. While Jude gazed at the man – his own grandfather – in wonder, Jessica took over the situation.

“H – Hi,” she breathed, “Are you John Winchester?”

The man narrowed his blood-shot eyes.

“Who's asking?” he snipped.

“Uh, we – we are. We're hunters, from Kansas. And we're trying to catch a warlock,” she carefully admitted, “We heard that you might have caught one, and we were hoping that you could tell us h – how you did it. Please. Someone we love is in danger.”

John looked between the two young adults with a very distrusting look in his eye. Jude almost thought that he was going to slam the door in their faces. But, instead, he momentarily closed it to unlock the chain lock. He reopened it a second later to reveal that he had been holding a shotgun in his left hand. He propped it up against the wall near the door and stepped to the side to nod toward the dimly lit motel room, offering them a chance to come inside.

“We'll talk in here,” he stated.

Jude shared a worried look with his cousin, who seemed equally nervous about entering the room. But they knew they had to do it. Jude didn't realize until he was halfway across the threshold that his and Jess's dads could possibly be in the room, too. As soon as he walked in, Jude scanned the entire place for two little boys, secretly hoping to catch a glimpse of his father and uncle at a younger age. There were toys and coloring books laying around, but no kids. Jude glanced at the closed door off to the side, wondering if Dad and uncle Sam might have been asleep in that room...

“Y – you have children?” Jessica cleverly prompted, pointing out a stuffed animal on the small couch.

Though he seemed hesitant to answer, John eventually turned around to face Jude and Jess after he closed the motel door behind them.

“Two boys,” he confirmed, though he didn't elaborate on it, “Who are you?”

“My name is Jessica. And this is my cousin, Jude,” Jess reluctantly admitted, gesturing to him.

Jude found it hard to meet eyes with his own grandfather. John had an unrelenting bold stare; the kind that pierced through you and made you feel hollow inside. His entire manner mimicked that of an angry and bitter old man who had no use for small talk. Geez, how could this guy be a father to two small boys?

“Jude, huh?” John repeated, glancing away, “My wife loved that Beatles song...”

Jude gulped and finally raised his head to look at John properly. Somehow, under all those layers of bitterness and hatred, there was a brief shimmer of honest emotion in John's voice when he said that. And Jude could almost see the sincere pain in his eyes when they looked at each other for the first time.

“... So does my dad,” Jude responded quietly.

They continued to stare at each other for a moment, and Jude could almost see the resemblance that his own father shared with the man he was speaking to now. But before his emotions could get the best of him, John carried on the conversation.

“You're trying to catch a warlock?” he repeated, getting back to the point.

“Yes,” Jessie answered, “He stabbed our uncle with a cursed blade and we need him to break the curse before it kills him. Can you tell us how you did it?”

John paused again to reach over and chug some beer from an open bottle on the table before leaning against it with his arms crossed.

“I did it by accident,” he began, “I've been trying to find a demon. He killed my wife a few years ago. I thought I could summon the bastard with a ritual spell I found in a book at the Memphis library. But I guess I read the Latin wrong, because some guy appeared in the trap and told me he was a warlock.”

“What did he look like?” Jessica asked, probably assuming that he was the same guy they were after.

“Short. Round. Crazy hair that stood up. Reminded me of one of those troll dolls that my boys carry around,” he answered, “That sound like your guy?”

Jude and Jessica shared a woeful look. Nope. That didn't sound anything like the man who stabbed Crowley.

“No,” Jessica denied, “Do you still have the spell? May we see it?”

John nodded and turned around to look among the books on the table. In the meantime, Jude searched the room for anything that might have been related to his own father. There were two small plates of half-eaten chicken nuggets on the counter – next to a couple rounds of shotgun shells. There were a few coloring pages of puppies and flowers on the table – but they were covered by open lore books and circled newspaper headlines. And by the door, there were two sets of small, colorful tennis shoes – overshadowed by the large, mud caked boots laying on top of them. It seemed like everything in the room that might have belonged to Dad or uncle Sam was covered up by John's hunting stuff. And it kind of made Jude upset. Why didn't John hang up those colored pages that his sons made for him? Why did he toss his ammo around right where his young children ate their meals? Why couldn't he keep his revenge-fueled grief to himself instead of letting it pour over his kid's lives too?

John eventually found what he was looking for and turned around to hand it over to Jessica. It was an ancient looking ritual book, property of the Memphis Public Library.

“I marked the spell for you. It's near the back. I checked that book out a few days ago, but you can return it once you're done with it,” John said.

“Thank you,” Jessica beamed, giving him a bright smile, “You have no idea how much this will help us.”

“No problem. I hope you catch the guy,” he shrugged, edging toward the door, “Is that all you needed?”

“Yes,” Jess said, taking hold of Jude's arm and toting him toward the door, “We're, uh, sorry for bothering you so late at night, Mr. Winchester. But we couldn't wait another minute.”

“It's alright,” John allowed, opening the motel door for them with a half smile, “You kids have a good night. Stay safe out there.”

“We will,” Jess promised.

As Jude made is way outside behind his cousin, he couldn't help but feel a twinge of panic. This was it. This was the only time he was ever going to be in the same space as his grandfather. Shouldn't he say something? Shouldn't he ask for advice or tell him something? Anything? Time was slipping away, and John was about to close the door forever! Jude's only chance to talk to his dead grandfather was coming to an end! He had to say _something_!

“I'm getting married soon.”

Jessica and John both paused to look at Jude, whose face was suddenly beet red in the dim light. He had blurted his sentence out loud and Jessica was staring him down with huge eyes, but Jude couldn't help himself. He had to say it. John was understandably confused, but bobbed his head in the doorway.

“Good for you, kid,” he muttered.

He raised his own hand to look at the gold wedding band that was still on his left hand before looking back up at Jude and Jessica with wise eyes.

“You two hold on to your spouses, okay?” he almost whispered, “Tell them you love them everyday. Take care of them. Believe me... You don't ever want to let 'em go...” 

Jude was unaware that moisture was blurring his vision as he nodded and backed away. For a brief moment, time didn't matter. It was just Jude, Jessica, and their grandfather speaking freely. Jude finally received the wisdom that he craved to hear from his late grandfather, and it was the most beautiful advice he had ever heard.

“I will,” Jude breathed, his voice partially stuck in his throat, “I promise.”

John smiled a little and nodded, before waving and finally closing the door. With the light from the motel room gone, Jude finally turned to face his cousin, who had also teared up. She sniffled and looked down at the book in her hand, which was shaking a little with her fingers.

“We... we got it,” she muttered.

Jude wiped his eyes and tried to get himself to focus again.

“Yeah. Let's go tell Papa,” he agreed.

When the kids turned to head back toward the main road, they stopped in their tracks. Jude's Papa wasn't standing where they left him. In fact, he wasn't anywhere in the immediate area.

“Where did he go?” Jessica breathed.

* * *

When Jude and Jessica made their way to the motel room to speak with John Winchester, Castiel slid under the shadow of a nearby tree to watch from a distance. The angel wanted to make sure that the children remained unharmed by their biological grandfather. Castiel knew from reading the man's journal that John Winchester's attitude toward strangers – and his own two sons – was far from friendly. At times, it was outright aggressive. But at the moment, he seemed to tolerate Jude and Jessica's unexpected arrival at such a late hour. He even welcomed them into his motel room without so much as an interrogation. Perhaps he was in a better mood than usual tonight.

Watching his son and niece disappear into the motel room made Castiel very uncomfortable. He disliked the thought of them being alone with John Winchester very much. But he supposed that they were of age and would be able to take care of themselves should John attack them. Or, at the very least, call to Castiel for aid. Once Jude and Jessica were inside, the angel that brought them was left alone in the dark. And his thoughts immediately gravitated to the one thing that always held most of his attention...

Dean.

The year was 1988, which meant that Dean was only nine years old at the current time. And Sam only five. Castiel's husband and brother-in-law were but mere children right now. But where were they? Surely they were inside the motel room with their father. But what of Jude and Jessica? Were they meeting their young fathers as well? Curiosity soon got the best of Castiel and he found himself walking around the building to get to the windows on the other side. He hoped that he would be able to peek inside the room and make sure that nothing abnormal was taking place. What he found instead was soft light shining through an open window – and two small children curled up in the same bed.

Castiel stopped in his tracks and gulped, seeing a tuft of chestnut hair spiked up from a pillow. Those soft strands could only belong to Dean Winchester. Somehow, the sight of Dean's extremely small form caused Castiel to abandon his entire regard for precaution. Though part of him knew that he could not interfere with things of the past, the angel couldn't help himself. He flew into the room to see the two children more properly.

Young Dean and Sam were bunched together on the white bed, which seemed large enough to swallow them. Sam was extremely tiny. It was difficult to believe that such a petite child would some day grow into the tall and stout man that Castiel knew. This younger version of Sam was almost buried into his older brother's side, fondly nestled close and sleeping peacefully... But Dean's posture was much less relaxed. The boy – merely nine years of age – was holding his brother with one hand, and loosely clinging to a gun with the other...

Castiel silently stepped forward to observe the scene at a closer perspective, feeling his heart break. The weapon on the bed appeared to be one of John's rifles. The safety was on and it did not appear to be loaded, but Dean was treating it the same way Jude used to treat his stuffed Bumble Bee; as if holding onto it brought him comfort. Castiel felt tremendous pain as he stared down at the younger version of his husband. Dean was so very young – so inexperienced, so undeveloped, so _innocent._ Most of the freckles Castiel memorized over the years had not even appeared on Dean's little round face yet. Time had not had a chance to mold his features; to tone his muscles, grow his facial hair, or probably even lower his voice. Dean was just _a child_ , and he was already clinging to a gun in his sleep. He was already taking full responsibility of his younger sibling and protecting Sam even as they slept. Though he was unconscious at the moment, Dean was still fully on guard. He wasn't completely at rest.

Dean was already a hunter at the fragile age of just nine-years-old.

The part that troubled Castiel the most, however, was that Dean's young face was skewed in his sleep. His tiny chest was heaving a bit, as if he was trying to catch his breath, and his eyes were flickering under their closed lids. During the countless nights that Castiel laid next to Dean, he had studied every aspect of his sleeping patterns. And now, as the angel gazed down at the boy on the bed, Cas was sure that Dean was having a nightmare.

Wanting nothing more than to ease the pain of his soul mate, Castiel leaned far over the bed to gently run his fingers through Dean's spiked brown hair. With his grace, Cas expelled the nightmare from Dean's mind and replaced it with a pleasant memory; one of Dean playing with his mother. After the discomfort faded from the boy's expression, Castiel very carefully lifted Dean's tiny hand away from the gun and placed it on top of his own chest, where it softly rose and fell with his tamed breathing. Afterward, Castiel pressed his lips to Dean's temple and indulged in his familiar scent.

“I will always watch over you, Dean,” the angel promised in a whisper.

Though Dean didn't know that it was said – and would probably never know – Castiel felt that Dean would eventually come to realize the honesty and meaning of the phrase in years to come. The precious boy on the bed had no idea how much was in store for him; all the love and adventure that life was going to offer him. There were so many people – so much family – he was still destined to meet, including his own son. Young Dean did have some rough times ahead, but the good certainly outweighed the bad tenfold. And for much of the time, Castiel would be right there by his side, making sure he would never face it alone...

“Papa?”

Castiel looked toward the open window at the sound of his son's distant voice. Jude and Jessica were wandering around the motel grounds, searching for him. Castiel took one last look down at the child on the bed, realizing how much he reminded him of their own son, before flying back outside to meet Jude and Jessica. The young adults both sighed with relief when they saw him, jogging over to his side with a book in hand.

“Where did you go?” Jude breathed, sounding a little frightened.

Castiel was hesitant to admit that he had visited Dean and Sam, because he was afraid that Jude and Jessica would request to see them as well and he did not want to startle John's children from their sleep. Instead, Castiel chose to keep the private moment to himself.

“Waiting for you,” the angel carefully stated, “Did John share the information you needed?”

“Yeah. I've got it right here,” Jessica nodded, holding up the book, “We can go back, now.”

Castiel nodded and turned to look at his son, who he assumed would be nervous about the flight back to their original time. Cas offered Jude an open arm, to which the young man slid in to hug the angel tightly from the side. Jessica took hold of Castiel's free arm as well. And once the seraph had both his son and niece in his grasp, he used the majority of his grace to transport them back to their current year. The flight took a few more seconds than normal, but they soon landed back in Robert Singer's salvage yard, next to a garage under a streetlight.

Jessica was the first to let go of Castiel. She unwound herself from his grasp and straightened her clothes before looking down at the book in her hands. A small giggle escaped her lips.

“This book is ridiculously overdue, now,” she mentioned.

Castiel only narrowed his eyes. The book was overdue? Overdue for what? After regaining his composure from the flight, Jude eventually let go of Castiel and chuckled in agreement. But Cas was lost. How could a book be overdue? Before he could ask the children what they meant, a voice called to them from Bobby's back porch.

“Jude?” Dean's gruff voice echoed toward the crushed cars, “Cas? Hello?”

“We're over here, dad,” Jude called back.

As soon as Castiel turned to see his husband walking toward them under the streetlight, all he could think about was seeing the little boy laying in bed, clinging to his brother and a gun. That same child, now an adult, was making his way toward Castiel with worry in his green eyes.

“What are you guys doing out here? I've been looking everywhere for you,” Dean grumbled in an anxious tone.

Before anyone answered him, Castiel stepped forward to meet his stride. Once close enough, he reached up to take hold of Dean's warm face and smile, admiring the sight of all the many freckles that were dotted along his cheeks and nose. After drinking in the view of Dean's familiar features, Castiel pulled the man in for a generous hug; wrapping him in comfort and affection. It was the hug that he wished he could have given to the same child back in 1988.

“I love you, Dean,” Castiel tenderly reminded.

Dean's arms slowly raised to hug Castiel in return, but the angel could tell that the man was confused by the sudden embrace.

“Uh... I love you, too..? What the hell's going on?” he asked.

At their side, Jessica held up the old book in her hand and smiled.

“We found a way to catch the jerk who stabbed uncle Crowley,” she informed.

 

**Notes for the Chapter:**

> Phew. How did you guys enjoy that little road trip to the past? ;D I know that this chapter seemed to throw a lot of info at you all at once, especially in the beginning with Rowena, but we will be sorting through it all as the story goes along. :) I'm sure that all my fellow nerds out there probably noticed the Lord of the Rings reference I made in this chapter, yes? XD Kingsfoil (aka Athelas) is the healing herb from middle Earth, the same that Aragorn used to slow Frodo's wound when he was stabbed with a Morgul blade in The Fellowship of the Ring. (It was also used by Tauriel in the Hobbit movie, when Kili was injured in Lake Town...) Oops. I geeked out there for a second. So sorry. Where was I? Lol! XD I hope that John's 'sudden willingness' to let strangers into his motel room in the middle of the night didn't seem to out of character. I just figured that Jess reminded John of Mary, and he couldn't possibly turn her away. :) And I'm sorry for the Dean feels near the end, there. I just couldn't let Cas visit the past without stopping in to see the chibi-version of his husband. ;) Thank you guys so much for reading and reviewing! I'm so glad that you are enjoying the story! :D The next chapter will be out soon! :)


	5. Chapter 5

When Jess, Jude, and Cas all got back from their trip to the past, they let Dean have a look at the ritual spell that grandpa John gave them. Of course, they didn't tell Dean where it really came from; just that they found the book among some of Bobby's old stuff in the garage. He was very impressed and relieved that they finally had a way to catch the guy responsible for hurting Crowley. Dean gathered Cas, Jude, and Jessica's parents into the kitchen and explained that the ritual spell should probably be done at the bunker, so that Caldwell would be trapped far away from Crowley and Clarence. Jessica could tell that Jude wanted to get back to the bunker because he knew he wouldn't be able to keep a secret from his fiance. And while Jessica really wanted to join and help them, she felt a dutiful urge to stay with uncle Crowley. After all, it was her fault that he was hurt in the first place...

Now, after receiving the first dose of Rowena's herbal healing medicine, Crowley was much more calm and reserved. Bobby and Clare had transferred him to the couch in the study and made him as comfortable as possible. The black wound on his stomach still looked awful – and was still spreading to the rest of his torso, but at a much slower pace. Rowena was kneeling next to him on the floor, constantly changing the dressings on his wound and feeding him some kind of green smoothie. Clare and Bobby were both walking back and forth from the room, bringing Rowena everything she needed to keep Crowley from being in too much pain. The sight of them working so hard to keep the poor guy alive made Jess feel even worse. All of this could have been avoided if she had just got rid of Caldwell when she had the chance. All she had to do was snap her damn fingers and the guy would have turned into dust. Why didn't she do it?

“Clarence, lamb, I'll need some more of this rose oil. There should be another jar outside in that storage crate near Robert's tool shed,” Rowena called as she dipped some gauze into her liquid concoction on the coffee table.

“I'm on it,” Clare breathed before spinning around and heading back out the kitchen.

Jess gulped as she watched her aunt Rowena carefully lift the white bandage from Crowley's side and reapply the fresh one. Crowley groaned out loud and gripped the back of the couch.

“ _Queen and country!_ ” he roared, glaring down at the spot on his stomach, “Do you have to be so _rough_ with that?!”

“Oh, pipe down, Fergus. The pain means it's working,” Rowena challenged, “Besides, aren't there more pressing affairs you should be worried about?”

“Like what, mother? Writing my bloody will? I'm a bit preoccupied with _dying_ at the moment!” Crowley barked.

“No, you ungrateful little swine!” Rowena hissed back, “I'm talking about Clarence! He deserves to know about his own father!”

“Oh, for Pete's sake,” Crowley grumbled.

At the sound of his name, Peter – one of uncle Bobby's hellhound mutts – popped his head up and barked toward uncle Crowley in question. The demon sighed and waved a hand toward the curious dog.

“N – no, not you,” he denied.

“Fergus, that boy is going to find out that he's related to that warlock one way or another,” Rowena continued, “It's best he hears the news from someone he cares for rather than on his own -”

“Spare me your incessant whining, woman. Can't you just let me die in peace?!” Crowley groaned.

Though the demon was probably trying to be funny, those words hurt Jessica's heart. She felt it seize up in her own chest as she knelt down on the floor next to Rowena.

“Uncle Crowley, I – I'm sorry,” she breathed, feeling tears swell in her eyes.

Crowley immediately lifted his head to look at Jess, where his brown eyes softened. He reached out a hand to rest on her shoulder.

“Come now, darling. Don't waste those tears on me. There's nothing for you to be sorry for – _Ow_!” Crowley gasped, glaring down at Rowena again, “ _Stop pressing so damn hard!_ ”

“Jessica, love, Fergie here is gonna be fine,” Rowena ignored Crowley's outburst to say, “I've slowed the curse down to a mere crawl. As long as I keep counteracting it with me own healing herbs, Fergus should last a few more days... And as for _you_ ,” she turned to look at Crowley again, “Why won't ya just tell Clare? Don't ya think he'll be cross with you for not tellin' 'em first? He'll be angry with you, Fergus! He'll be downright furious! Just tell 'em Caldwell is his father!”

“ _No!_ ” Crowley shouted, his eyes flashing solid black, “That bastard is _not_ Clare's father!”

The wounded demon paused again to raise his hand and point toward the other side of the house, where Bobby was digging something out of his supply closet.

“ _He_ is!” Crowley muttered in a serious tone.

Jessie swallowed again and glanced between Crowley and her uncle Bobby in the hallway. She felt like she understood what her uncle was saying. Bobby might not have been physically related to Clarence, but he was still Clare's father. He took him in, gave him a home, fed him, taught him, loved him. Bobby was Clare's father. And so was Crowley. Jess looked back to the demon on the couch with her head tilted a bit. Why didn't Crowley include himself when talking about Clare's parents? Under Jess and Rowena's stares, Crowley exhaled and rolled back to stare up at the ceiling as he held his own side in pain.

“Bobby Singer is the only parent he'll ever need,” the demon finished.

“That's a load of bollocks, Fergus,” Rowena murmured, “He'll need you, too.”

Before Crowley could properly argue with his mom, the back door opened in the kitchen and Clarence came jogging back in. He held a jar of pink oil toward Rowena and she accepted it with a warm 'thank you.' Jessica could feel the hidden tension in the air as Crowley and Rowena eyed each other in Clare's presence. It was clear that they were both still fighting without saying words.

“Is, uh... Is he going to be okay?” Clare asked.

“Of course he is, lamb,” Rowena promised with a nod, “It'll take more than a wee poke with a toothpick to take down a massive hog like Fergus.”

“Bugger. Off. You. Sourly. Bitch,” Crowley barked each word angrily.

Clarence and Jessica both shared a small smile with each other. As dire and stressful as the situation was, it was nice to hear Rowena and Crowley sassing each other like a true mother and son.

“Crowley,” Clare said, crouching down near the sofa to speak only to him, “Don't go dying on me, alright? I've got a wedding coming up and I need someone to usher people to their seats.”

Jessica smile grew a bit, seeing humor appear on Clare and Crowley's faces. Clare was obviously just joking about the usher thing, but was still serious about the wedding...

“Not to worry, boy. I'll be there...” Crowley muttered.

Though his words were honest, Crowley's tone was very saddened. It almost sounded like he wasn't sure if he would make it or not. Before the sting of his heartbreaking voice could register with the other people there, Bobby came back into the study with a bundle of pillows.

“Clare, help me put these under him,” he asked.

Jessica and Rowena scooted out of the way so that Bobby and Clare could arrange some pillows around Crowley. The demon groaned and winced the whole time he was being moved, but he eventually settled down once they were done. He looked absolutely comfortable afterward, surrounded in fluffy cushions and blankets from home. The sight made Jessica feel a little better. He might have been hurting, but at least he was cocooned in love.

“How's that, darlin'?” Bobby asked.

“Perfect, dear. Thank you,” Crowley sighed, squeezing his eyes closed, “Mother, I can feel it spreading.”

“Clarence,” Rowena called, pulling him down into the floor with her, “Help me soak these gauze, love. We've got to keep alternating them. Jessica, cherub,” she paused to turn toward Jess, “Everything is under control here. Perhaps yer fathers would like some help back at the bunker, hmm?”

Jessica exhaled and nodded. Rowena was right. Everything seemed to be okay here. Crowley was stable and well taken care of by his family. If Jessica really wanted to help him, she needed to catch the jerk responsible and make him break the curse. Before she left, Jessica stepped over and squeezed Crowley's hand.

“I'm gonna get the guy that did this to you,” she promised.

Crowley smirked back at her from the couch.

“That's my girl,” he winked, “Off you go, lass.”

With one more firm nod, Jessica flew herself away from Bobby's house and landed back in the bunker. She ended up in the study, where a few piles of books were laying open – and Dickie was humping his moose. The dog was riding the poor stuffed animal under a table, but stopped when Jessica appeared.

“Sorry for interrupting,” Jess whispered, noticing that the place was empty, “Where is everyone?”

Dickie gave a single bark, turned to pick up his stuffed moose with his mouth, and started walking for the entrance of the library. Jessica followed her Papa's dog all the way through the bunker, out of the control room, passed the kitchen, by the bedrooms, and down the hall, where a few stairs led to the darkest part of their home. It was the lower level, where the old offices, storage rooms, and the dungeon were. Dickie paused and wagged his tail by the door of the 'dungeon', where she could finally hear voices coming from inside. Jess smiled and reached down to pet Dickie on the head.

“Thanks, boy,” she praised.

Dickie wandered off with his stuffed moose again while Jess opened the door to get to the rest of her family. When they first moved into the bunker, Jessica was never allowed to step foot in this room. The 'dungeon' was off limits to her and Jude for a long time, until they got older. Their parents used it to hold and interrogate all kinds of monsters and beasts. In fact, they used it so much that uncle Bobby helped them build a wall through the center of the room that had a two-way mirror. It gave off a police vibe, but it got the job done ninety percent of the time. Right now, both doors were open and all of Jessica's guys were reading from grandpa John's book and discussing how to set up the ritual spell.

“... Purified water, Rosemary, and – Garlic salt? Really?” Jess's Papa scoffed, “What are we doing? Catching a warlock or making a fancy meal? Should I wave a wand or use a whisk?”

“Gabriel, this is no time for your childish antics,” uncle Cas warned, taking the book from his hand, “We must apprehend this warlock as soon as possible, no matter how odd the ritual sounds.”

“Cas is right. I've seen way crazier spell ingredients than that,” Dean agreed, “What we really need to focus on is the sigil.”

“Yeah, we have to make sure that none of the lines are broken. Which is why I'm suggesting we use spray paint, this time,” Jess's dad added.

“Fine. How long do you guys think this will take?” Pop asked.

“Eh. Maybe an hour or two,” Dean shrugged, “It says we need Raven feathers, which means Cas and I are going to have to catch -”

Jessica's cell phone started ringing from her pocket, which made her flinch in surprise and cause all the guys to look toward her. The song was 'Lollipop' by the Chordettes, which meant that it was Ollie calling. Oh! Ollie! It felt like forever since Jess talked to him! And, man, did she have a lot to tell him about. Jess excitedly patted around her jacket until she found her phone and dug it out. She turned away from the rest of the guys before she answered it with a smile.

“Hello?” she asked.

“H – hey, Jess,” Ollie began, his voice kind of high and nervous, “Um, what are you doing?”

A million things flew through her mind – from the incident at the lounge, to finding out about Clare's dad, to helping uncle Crowley, to going back in time and meeting her grandpa John, to making a ritual to catch a warlock. So many things had happened! How was Jessica supposed to tell him all those things?

“Uh... you know. Just hunting things. Saving people,” she casually summed up, “What about you?”

“I just got out of class. But the reason I'm calling you is because... Well, do you think you could, uh, meet me for lunch? In about an hour?” He asked.

Ollie hadn't sounded this nervous in years. Was something wrong? About the time she thought this, her parents both walked around to shrug their shoulders in question. They obviously wanted to know who she was talking to and what was going on, but Jess was more focused on Ollie.

“Sure. Of course,” she instantly agreed, “Is everything okay?”

“Y – yeah. I mean, everything is great. Better than great, actually,” he chuckled anxiously, “Um, I was going to take you to that Mexican place you like. The one near the Shell Station. I know it's your favorite... I, um, I wanted it to be just you and me but, my mom wants to come along... I hope that's okay...”

Jessica gulped as she stared up at her confused parents. Everything was slowly making sense. Ollie's nervousness, the fancy restaurant, wanting to be alone... This was it! Ollie was going to _propose_! _He was going to ask her to marry him!_ For a moment, Jess forgot to speak. She just stood there like a smiling idiot while her parents stared at her.

“What? Jessica, what is it?!” Papa asked.

“Jess?” Ollie asked on the phone.

“Y – Yes! _I do!_ ” Jessica suddenly shouted, before gulping and dialing it back, “I – I mean, um, I do want to have lunch with you! And it's totally fine if your mom is there! In fact, Dad and Papa might want -”

“Oh, I was hoping that it could just be you, me, and mom,” Ollie interrupted, “This is, um, kind of important and I'm already nervous about it, and... Well, your dads make me more nervous, so...”

Jessica giggled. This was so sweet! Ollie was acting just like Jessica knew he would when it came time for their engagement. And she totally understood where he was coming from when he mentioned her dads making him nervous. Dad alone was enough to make Ollie feel uncomfortable.

“That's okay. Sounds great,” Jessica agreed, “So, I'll meet you there in an hour? Does that sound good?”

“Sounds perfect,” Ollie added, “I'm excited to see you, Jess. Thanks. I love you.”

“I love you too, Ollie,” she grinned, “Bye.”

“Bye,” he repeated.

When the phone went dead and Jessica lowered it, her Papa grabbed her by the shoulders.

“What's going on? Is the gingerbread man okay? Why did you mention me and your dad?” Papa asked in an excited blur.

“I – I think this is it,” Jess admitted, “I think Ollie is going to propose to me.”

Both of her parents gasped in shock, although Dad's was a little less happy than Papa's.

“Wait, Oliver wants to propose to you? _Today_?!” he asked.

Jessica giggled and nodded. It sounded so much better out loud! She and Ollie were about to be fiances, just like Jude and Clare! Papa squealed and jumped up and down, pulling Jess's arms to make her do it too. For a second, she and her Papa just giggled and jumped around like a couple of teenage girls. Ahh! She was getting engaged! This was going to be so great!

“My baby bunny is going to get married!” Papa sang, “Moose, go get some nice clothes on! We're gonna go watch our -”

“Actually, Pop,” Jess interrupted, “Ollie doesn't want you guys to be there.”

“ _What_?!” both of Jessica's parents gasped in offended unison.

Jessica nervously shrugged.

“He said that you guys make him too nervous,” she admitted.

“Ah, great. This is all your fault, Sam! You went and scared the kid, and now we won't get to watch our baby get engaged!” Papa grumbled.

“But, I haven't done anything!” Dad disagreed, “I mean, okay, I ruined their first dance. But that was ages ago! I'm totally fine with it, now! Jessica, you know I'm fine with you being with Oliver, right?”

“Um... I guess?” Jess muttered.

“Then can we please go and watch you get engaged?” Dad asked.

Jessica felt torn. Of course she wanted her parents to be there, but if it scared Ollie into not asking her to marry him, then what good would it do? Her hesitation must have been written on her face, because Papa seemed to understand. He paused to look around and think.

“Alright. Oliver doesn't want us there, but you do,” he guessed, “I've got it! Sam and I will just hide somewhere close by, preferably in drag -”

“No drag,” Dad blurted.

“ - and that way, we get to see you without him seeing us! It's a win-win!” Papa grinned.

“But what about Crowley?” Jessica suddenly remembered, “What about the ritual spell?”

“Don't worry, Jess. The spell is going to take at least a few hours to put together,” Dad replied, “It's plenty of time for you to meet Oliver.”

“And get engaged!” Papa squealed again, “Oh, I can't wait! My lil' honeydew is going to be a bride!”

Jessica giggled again, feeling a fresh wave of happiness flow over her heart. Papa was right. In just an hour or two, Ollie was going to be her fiance! And she couldn't wait for it to happen, and share the love with her whole family.

“Okay. You guys can hide out and watch,” Jessica allowed, “Just don't let Ollie see you.”

“Sweetheart, we're as good as invisible,” Papa promised with a wink.

* * *

Jessica was so eager to meet her boyfriend for lunch that she almost forgot to change clothes. She was still wearing the same outfit from the day before – because their family's late night warlock catch went horribly wrong and she hadn't had time to even look at herself in a mirror, let alone change clothes – so she basically flew herself to her room to pick out a new outfit. This time, she threw on her fanciest black dress that laced up in the back, and a pair of shimmery heels. She wanted to look absolutely perfect for her engagement night, just like Jude and Clarence looked on theirs. Changing clothes actually made her wonder what Ollie would be wearing. Would it be the nice outfit that his mom bought him for graduation? Or maybe even a three piece suit? Oh, wow, just the thought of Ollie looking so handsome made her blush.

Once she was ready, Jess met up with her parents in the control room – where they highly praised her and reminded her of how beautiful she was – before flying to the Mexican restaurant to wait for Ollie. Dickie invited himself too, as usual, and sniffed around a dumpster in the back alley as his three humans walked around to the front of the restaurant.

“Remember what I said. You can't let Ollie see you,” Jessica hissed as she led the way.

“Don't worry, baby bunny. Your dad and I are masters of disguise. And we're gonna do the drag thing, right, Sammy?” Papa winked.

“No we are not,” Dad disagreed, “We're just going to act natural and stay out of – Gabe! What the hell?!”

Jess paused to look back – and saw her Papa dressed completely in pink. He had fashioned himself a curly blonde wig, put on make up, and was wearing a pink skirt. There was even a bra outline under his low cut top. Jess couldn't stop the few giggles that escaped her mouth. Papa looked hilarious! He didn't even shave his stubble! He was clearly just a man in feminine clothing.

“There's no need to use that tone with your beautiful wife, Sam Winchester,” Papa said, adjusting his nonexistent boobs.

“I don't have a wife. I have an obnoxious husband who loves to embarrass me,” Dad replied, crossing his arms, “C'mon, Gabe. That's not necessary.”

“Necessary? No. Useful and Fun? Yes,” Papa argued, turning his attention to Jess, “Bunny rabbit, your father and I are going to hang out by those trees right there near the entrance,” he paused to point to them, “and when you guys go inside, we'll casually follow you and watch from the shadows, alright?”

“Okay,” she nodded, “Bye, mom and dad!”

Jessica and her Papa both giggled, but Dad only rolled his eyes. He obviously didn't enjoy Papa being in drag as much as they did. With her parents safely hidden in plain sight, Jessica wandered over to stand by the sidewalk and wait for her boyfriend and his mother. She couldn't stop the butterflies from swarming in her stomach. Any minute now, Ollie was going to arrive with her wedding ring in hand. Oh, he was going to get down on one knee and propose! _Stay calm_ , Jess told herself, _You have to act surprised when he does it_.

After what seemed like forever, Jessica finally caught sight of Ollie's car pulling into the parking lot. Ms. Jane must have caught sight of her too, because she smiled brightly and waved. Jessica waved back, feeling so excited to see her future family. She dashed over to open Ms. Jane's door for her, wanting to help her out. In the meantime, she glanced inside to see that Ollie was very pale and fidgety; as nervous as a Chihuahua at the vet.

“Ah! Guapa!” Ms. Jane sang as she stepped out of the car to hug Jess, “Oh, it's been such a long time! You look beautiful!”

“Thank you, Ms. Jane,” Jess hummed, feeling her own face glow with warmth, “So do you!”

“Oh, gracias, Jess. You are so sweet,” Jane replied with a giant smile, “Oliver just picked me up from work for lunch, so I probably look a little frazzled.”

Jessica was going to deny that Ms. Jane looked anything other than perfect when Ollie stepped around the vehicle. He was wearing a really nice polo shirt and a pair of jeans, but his hands were twitching a lot at his sides. Jessica could see that he was painfully nervous. His face was extremely pale under his freckles and his brown eyes were attached to Jessica's form. It seemed like seeing her made him feel a little bit better, and Jess was relieved. She didn't want him to be nervous. Not for something as special as this.

“Hey, Ollie,” she hummed.

“H – Hi,” Ollie barely got out.

Ms. Jane seemed to be under the impression that the three of them were only going to have lunch. The older lady must have been out of the loop about the whole proposal thing, because she was already deciding what food she was going to order.

“I have been craving some guacamole and chips,” she hummed, starting to walk away, “I might even have myself a Margarita before I go back to work -”

“Wait!”

Jessica and Jane stopped in their tracks and turned back to face Ollie. The jittery redhead was loitering by the back of his car, chewing on his bottom lip and staring hard at Jess. She blinked back at him, wondering why he wanted to wait.

“I... I'm not going to make it in there,” he admitted with a large gulp, “I have to do this now.”

Jessica's heart nearly leaped from her chest. Oh. Oh! Ollie was going to do it right now! He was going to propose right now! Jessica felt the urge to turn and look for her parents, to see if they were watching, but she couldn't turn her head. She was too focused on Oliver's lovely brown eyes.

“Do what, Ollie?” Jane asked, sounding lost.

First, Oliver took a breath and looked down at his feet. It gave Jessica a chance to clasp her own trembling hands together so that she didn't look so nervous. When he finally got up the courage, Ollie raised his head again to look straight at her.

“Jessica,” he started, voice low.

“Y – yes?” she replied, holding her breath.

Ollie glanced at his mother once before saying -

“... I'm dropping out of college.”

For five solid seconds, the entire parking lot was silent. The word 'yes' had been teetering on the edge of Jessica's mouth, but now she had to swallow it very hard. Wait. What? Ollie wasn't proposing? He was going to _drop out of college_ instead?! That's what he brought her here to say?!

“ _What?!_ ”

Oliver, Jane, and Jessica all turned to look toward the entrance of the restaurant, where Dad and Papa were now completely facing them in broad day light. Papa – still dressed in drag and holding Dad's hand – flew across the parking lot, popping both of them near the rest of the group in an instant. Jessica's parents were both wearing angered scowls and open mouths.

“Oliver, you can't drop out of school! That's a terrible decision!” Dad breathed in shock.

“Drop out of college?! No! You can't do that! You just started your pre-law classes!” Ms. Jane added.

Ollie jumped at all the shouting and raised his hands in defense, but narrowed his eyes toward Jess's parents.

“Wh – what are you two doing here?” he asked, “I just wanted to tell mom and Jess!”

“Well, we didn't know you were going to deliver such idiotic news!” Papa griped, “Carrot-top, you can't turn your back on your education. Your mom is helping you pay for it and everything!”

“I know that!” Ollie nearly shouted back, though he was still fidgeting with his own nervous hands, “And I'm going to finish paying for the classes I've taken, but I can't do it anymore -”

“Do you need a tutor or something? Are you getting behind? I can help you, man! I was pre-law, too,” Dad offered kindly.

“No, I don't need a tutor,” Ollie denied, “I just need -”

“You need to go to school, Oliver!” his mom barked, planting her hands on her hips, “You're going to have the education that I never had. That's why I'm helping you do this! You cannot give up!”

“I'm not giving up, mom. I just don't want to be a lawyer, okay?” Ollie said.

“Then just change your major, kid!” Papa pointed out, pausing to brush some of the fake blonde hair out of his face.

“If you don't want to be a lawyer, what _do_ you want to do?” Dad asked.

“Oi, don't you dare say you want to be a baseball man!” Jane warned, “Your father is always going on about that stupid game! Do I need to call him, huh? Is he the one filling your head with this craziness?!”

“No!” Ollie groaned, “I don't want to play baseball either! I want to do something that will actually help people. I want to be _a hunter_ , okay?!”

Jessica gulped and glanced toward her parents, who were already wearing stunned expressions. Uh-oh. This wasn't going to end well...

“Y – You want to be a hunter? _A hunter_?! Are you out of your mind?!” Dad blurted in exasperation.

“Oliver, you cannot do what these men do!” Jane nearly shrieked, “They kill things for a living! Remember that time it was dark and we almost died?! They do those things every day! I will never let you do that!”

“We're with Jane on this one, kid,” Dad huffed, “Hunting is dangerous. Why do you think Jess and Jude never went to school? Because people wanted to kidnap and kill them! Hunting is no life to live. Believe me.”

“I've done it with you!” Ollie reminded, “I was there when Jude flew for the first time! I was there when we took on the darkness! I can help! I can save people! I can be a hunter!”

“Oliver Edwardo Thompson, I will hear no more of this foolishness,” Jane snapped, “You are going to finish school, get a reasonable job, and put away all these outrageous dreams!”

Ollie sighed and looked down at his hands again. Everyone was quiet as they watched him reach into his pocket and pull out his car keys. He sat them on the back of his car and finally raised his head to look at his mom.

“It's too late. I've already signed the papers,” he admitted under his breath, “I'm going to tell dad that I won't be going to the batting cages either. He's going to be pissed at me, too... I'm sorry. I just can't live my life for other people anymore.”

After his solemn words, Ollie turned around and started walking away without even saying goodbye. He had left the keys for his mom to take his car. And even though all the adults were shouting for him to stop and come back, no one went after him... No one except Jessica.

Though her heart was broken and her chest was full of anxiety, Jessica raced up to slip her arm around Ollie's. He paused to look down at their joined arms before looking up to search her face with hopefulness. Jessica was disappointed that her proposal didn't happen today and she didn't quite agree with Ollie's choice to drop out of school. But right now, Oliver didn't need a lecture or guilt trip. The only thing he needed was a friend; someone who would listen to him and give him a chance to speak. Someone to help him make choices and feel better. He needed his soul mate. He needed Jessica.

“I'll walk with you,” she offered in the most calm voice she could muster.

Ollie looked like he was suddenly on the verge of tears. His shiny brown eyes gazed at Jess with warmth and relief. His hand slid down to clasp hers tightly as they walked in stride with Dickie roaming around their feet.

“Thank you,” he whispered.

 

**Notes for the Chapter:**

> ...yeah. So, Oliver's dream is to become a hunter. Bet you didn't see that coming, did you? (Oh, who am I kidding. You probably did. Lol) XD I know that this last part was probably a total let down to everyone involved, (including us readers) but Ollie's inner conflict is just another thing we will be working through in this story. :) And it might not seem like it from all the name calling, but Crowley and Rowena do love each other. At least a little bit. Lol! XD I know there wasn't much plot going on in this chapter, but I hope it didn't stray too far from the main story. We will be picking back up with the ritual next week. ;) Thank you guys so much for reading and reviewing! The next chapter will be out soon! :)


	6. Chapter 6

When his parents finished preparing everything they needed for the ritual that would summon the warlock responsible for hurting Crowley, Jude opted to wait upstairs until the whole ordeal was finished. He didn't want to be anywhere near the jerk, let alone watch his parents try to force the guy into breaking a spell. 'Hard persuasion' was one of the few things Jude actually hated about being a hunter. Forcing someone to do something, especially through means of violence that border lined torture, wasn't in Jude's nature. No matter how much that person may have deserved it.

Of course, Dad and Pop assured him that it was okay if he waited upstairs. It seemed like they didn't want him to witness the act anyway. So, while his father rehearsed the Latin speech in the library book and his Papa stood guard near the sigil on the floor, Jude quickly escaped the 'dungeon' and headed upstairs to the kitchen. It wasn't because he was hungry or anything. The kitchen just felt like the warmest, safest place in the bunker; somewhere he really wanted to be at the moment. Keeping such a huge secret from Clarence made Jude's stomach hurt in all the wrong ways, and he hoped to find comfort in his favorite spot of home.

All of the food that Jude had been cooking earlier was still laid out on the stove. None of it was probably edible by now, so Jude decided to make himself useful and clean up the mess. He felt painfully lonely as he cleared and washed the dishes in the sink. Nearly an hour of silence went by before someone else entered the room. The 'whoosh' of someone flying in made Jude turn around as he was drying his hands. He was extremely relieved to see his two best friends standing in the doorway. Jess and Ollie – both wearing nice clothes – had their arms linked, but their expressions were pained. Neither of them even smiled when they looked up to see Jude. Wow. He thought that Ollie and Jess were going to get engaged, but something bad must have happened...

“Hey,” Jess muttered to Jude as she ushered her boyfriend to the counter and let go of his arm, “Ollie, I'll be right back, okay?”

“Okay,” Ollie replied blandly.

Jude shared a questioning look with his cousin, hoping to figure out what was going on between her and their mutual red-haired friend. But she only shook her head in disappointment and wandered out of the kitchen. Jude assumed that she was either going to check on the ritual in the basement or just needed a moment to herself. Either way, her absence left Jude and Oliver alone for a minute and Jude was rather comforted by the notion. Talking to Ollie seemed like a very good distraction from all the horrible things going on.

“Hey, man,” Jude started, “What's going on?”

“Nothing,” Ollie sighed, leaning against the counter and staring down at the floor, “I just... dropped out of college.”

“Oh,” Jude murmured.

That explained a lot. Maybe the reason Ollie and Jess were so upset was because dropping out of school was a difficult decision or something. Jude had never gone to school, so he didn't know how big of an impact it had. Still, the understanding tone in which Jude said 'oh' seemed to make Ollie feel a little better. He raised his head to finally look Jude in the eye.

“Yeah...” he nodded, as if that summed up everything he was feeling, “What about you?”

The first thing that came to Jude's mind was the ritual happening down stairs; how his family was trying to capture a warlock – that may or may not have been Clare's actual father – so they could make him break a spell before Crowley took a turn for the worst... but all of that stuff seemed too heavy to bring up. Jude didn't want to talk about bad stuff and it seemed like Ollie didn't want to either. Maybe this was a good time to tell Oliver about the only good news that had happened to Jude in the last two days.

“Clare asked me to marry him,” Jude admitted, briefly flashing the shiny new ring on his finger.

Ollie glanced at the ring, but didn't smile.

“Oh yeah. Jess told me about that,” he nodded a bit.

Jude found his friend's reaction a little strange. Ollie didn't say 'congratulations' or anything. Was he not happy for Jude? Or did he just not like the idea of engagements right now, because of the whole school thing? Was that the reason why he hadn't asked Jess to marry him yet? Jude felt compelled to ask these questions, but was a little nervous. Maybe Ollie didn't want to talk about it...

While Jude struggled to keep the conversation with Ollie going, movement in the kitchen doorway caught his attention. He looked up to see his dad standing there, looking very distraught. With his eyebrows furrowed and mouth turned downward, he met eyes with Jude and casually gestured for him to come out into the hall. Jude gave Ollie a pat on the shoulder as he passed by to join his dad outside. He assumed that Papa was still in the 'dungeon' with the ritual stuff, because Dad was alone.

“Hey, little man,” Dad muttered when Jude was close enough to hear.

Jude gulped. Little man? Dad hadn't called him that in a while...

“What's the matter?” Jude nearly blurted.

Dad took a deep breath and rubbed his forehead before speaking.

“We caught him. He's downstairs, in the trap,” Dad admitted, his hollow voice giving Jude chills, “and just from looking at him, I'm eighty percent convinced that he _is_ Clare's dad. He's got the blonde hair and everything.”

Again, Jude felt like he had been kicked in the gut. On some level, he really hoped that it wouldn't be true. But if Dad was this sure about it...

“The thing is, he's as stubborn as a jackass. He won't comply with anything. Hell, he even told us to go ahead and kill him,” Dad continued, his eyebrows lifting a bit, “and I'm afraid that might be the only option we have left...”

“K – killing him?” Jude breathed.

Dad nodded and took another breath.

“I know it sounds grizzly,” he allowed, “but I'm pretty sure that if we kill the bastard, the curse will break too. He dies, Crowley lives. And the guy's already trapped in our basement, where we can end it quick and quiet... the only thing is... Clarence...”

Jude could practically hear his heartbeat in his own ears. He knew what his dad was getting at. Was it fair of them to kill Clarence's father like that? Without even telling him about it? Jude couldn't be a part of that! Dad must have seen the anguish in Jude's eyes because he rested a hand on his shoulder.

“Jude, you know Clare better than anybody else,” he breathed, “Do you think he would want to know about his father? Or should we keep him in the dark until it's done? I'll leave the decision up to you, buddy. You're his fiance…”

Jude bowed his head and blinked at the floor. He thought it was very nice of Dad to wait and see what everyone else thought before he killed the warlock. But being saddled with such a large decision made Jude ache inside. Of course he knew that the right thing to do was tell Clarence everything. Clare had every right to know about what was really going on. But what if telling him only led to more heartache? Was it better for him to know all the facts and be burdened with the pain, or to remain blissfully unaware of everything? Though happy ignorance was a tempting choice, Jude knew he had to do the right thing. No matter how much it hurt...

“I've gotta tell him,” Jude finally replied.

Dad didn't judge at all. He calmly agreed with Jude's statement and patted his shoulder again.

“Okay,” he allowed, “Go get him and bring him back here. Papa, Sam, Gabe, and I will wait down in the basement for you.”

Jude bobbed his head, but felt the tug of hesitation in the rest of his body. His first instinct was to panic a little at the thought of flying all the way to Bobby's house by himself. But knowing that he was going to fly toward Clarence made him a bit more confident. It gave him a reason to calm down and focus. Plus, Dad lingered near Jude and waited for him to go, probably sensing his unease. Dad's presence actually helped Jude close his eyes and picture uncle Bobby's kitchen in his mind...

And when he opened them again, Jude was standing near the kitchen table. He was facing the study where Rowena, Bobby, and Clarence were all situated around Crowley, who was laying on the couch. Bobby was holding his hand, Rowena was laying some sort of wet gauze over his stomach, and Clare was kneeling near the coffee table, preparing more bandages. Jude paused and stared at the back of his fiance's blonde head for a moment, wishing he didn't have to disturb him. Clare looked so determined and proud to be helping Crowley feel better, and Jude hated that he would be the one to stir up Clare's emotions.

“Clare,” Jude forced himself to call.

As soon as the handsome demon spun around and saw Jude in the kitchen, a relieved smile blossomed on his lips. Ignoring everyone else's stares, Clarence sat down his work and climbed to his feet to meet Jude.

“God, Jay, are you alright?” he breathed, worriedly running a hand through Jude's hair, “Bobby told me you went to help your folks with that ritual. Did you do it? Did you catch the asshole that did all this shit?”

Jude swallowed the moisture in his mouth as he stared at Clare's large and lovely eyes. Oh boy. How was Jude supposed to explain everything to him? There was a small grunt from the study that briefly pulled their attention back to Crowley. The king of Hell had shifted on the sofa, but his eyes were zeroed in on Jude from a distance. He obviously didn't want Jude to tell Clarence the truth, but Jude couldn't stand keeping it a secret anymore. Clare deserved to know.

“I have to tell you something,” Jude nearly whispered, tugging Clare closer by the front of his fabric jacket.

“Alright,” Clare replied in a concerned tone, “What is it?”

Jude glanced back into the study, where Crowley was still giving him that wincing, pleading look, before closing his eyes completely. He imagined one of the bunker hallways in his mind; an empty place where he and Clare could talk in privacy. With a tiny spark of his grace, Jude flew them there. The motion of flight didn't disturb him nearly as much as the shock on Clare's face.

“Whoa. Why'd you bring us here?” he asked.

“Dad and the others trapped the warlock. He's down there, in the basement,” Jude finally began, gesturing toward the staircase nearby.

“Good,” Clare spat, “Did your dad beat the curse breaker out of him yet? Crowley doesn't have much time.”

Jude took a breath to steady his own thoughts. Would Clare's tone be just as hateful if he knew he was speaking about his own relative?

“No. He won't say anything. Dad says that killing him is the only option we have left,” Jude explained.

“Then what's the damn hold up?” Clare breathed.

Jude gazed into Clare's eyes for a second, wishing there was some other way to break the truth to him.

“He's... He's your dad, Clare,” Jude finally admitted, “The warlock. He's the same one that... that kidnapped your mom and stuff.”

At first, it seemed like Clarence didn't believe him. The blonde demon shook his head back and forth and wore a doubtful smile.

“No, Crowley said he killed him, remember?” he replied, “I don't know what kind of bullshit that warlock's been feeding you guys, but -”

“Crowley was the one that confirmed it, right after he got stabbed,” Jude quickly recited the story he was told, reaching out to take Clare by the hands, “Clare, I know this is probably hard to hear... but that guy down there in the basement is your father. And the only reason he isn't dead yet is because my dad wanted to give you a chance to know first. I'm – I'm not pressuring you to do anything you don't feel comfortable with,” Jude reminded, as he reached up to touch the demon's cheek, “I just wanted you to know, because he's trapped in the basement right now and this might be the only chance you get to see him. If you want to.”

The same emotions that stirred in Jude's heart when he saw his grandpa John were leading him to encourage Clare as well. Of course Clare's dad was a piece of work, but maybe Clare had some things he wanted to say to him. Maybe there were some questions he needed answers to, or some anger he wanted to work through. Or maybe he just wanted him dead like everyone else. Jude had no idea how he was feeling. A few moments ticked by, in which Clare almost stared through Jude in thought, before he seemed to come back to himself. All the humor had fled his face and he seemed calm and serious.

“... Okay,” he murmured above a whisper, “I just want to look at him, first...”

Jude immediately nodded and squeezed Clare's hand, giving him the most reassuring expression possible. Taking his fiance's request to heart, Jude turned to lead Clare down the staircase next to them. Clare walked at a very slow pace, probably still trying to wrap his head around the thought of his father being alive and within reach. Jude kept a close eye on him all the way to the entrance of the dungeon, where they both paused and looked at each other before venturing inside.

Just like Dad promised before, he, Papa, Sam, and Gabe were waiting on them inside. Although, now, Jess and Ollie were there too. The six of them were clustered by the two-way mirror that uncle Bobby helped them install a few years ago, stealing peeks into the other room while they whispered to each other. It took a second for them to notice Jude and Clare walk inside, but once they did, apologetic and apprehensive expressions flashed on their faces. The four adults looked especially worried to see Clare. In the awkward silence that settled among everyone, Jude could hear a distant voice. Someone – probably the warlock in the next room – was singing very loudly. It sounded like the original French version of 'Frere Jacques', and it was being sung masterfully well...

“Hey,” Jude's dad finally broke the tension to say.

Though the greeting was directed at Clarence, the demon didn't respond. Instead, he started taking slow steps through the small crowd to get to the mirror across the room, gently pulling Jude along by the hand. Jude, of course, followed his love to the window, where they both peered in and saw the warlock for the first time.

Dad was right. The man bound in the trap did look a lot like Clarence. His hair was the same shade of blonde; thinner, though, and a bit shorter. The structure of his face resembled Clare's, right down to the dip in the middle of his chin and the faint tilt of his nose. His eyes, however, seemed to be an eery shade of brown-ish red; almost maroon. But the most distinct feature of all was the very long scar that ran from the top of his cheekbone all the way down his neck, into the collar of his shirt. The warlock was sitting in a chair in the middle of the sigil, swaying back and forth with his arms crossed as he sang to himself. The guy didn't seem distressed in the least. On the contrary, he seemed at ease with his current predicament of being held hostage.

After taking a good look at the odd man beyond the glass, Jude brought his attention back to Clarence. The demon observed the warlock for a few extra moments, his eyes shifting between emotions, before taking a step back. Everyone else in the room was quiet, waiting to see what Clare's reaction was going to be. Eventually, Clarence opened his mouth without looking away from the window.

“What's his name?” he asked.

“Caldwell,” uncle Sam answered.

“Caldwell? More like 'Cock-smell', am I right?” uncle Gabe muttered, giving Sam a nudge and a wink.

Though Gabe was attempting to lighten the mood with a joke, all the other adults shot him a foul glare.

“He's from Europe, and he's apparently very old,” Jude's dad informed, dismissing Gabe's comment, “Crowley was trying to catch him because he's been kidnapping female demons again, but he got away after he stabbed him. We've been trying to get him to tell us how to break that damn curse, but he's not budging... You wanna give it a shot?”

Clare finally turned away from the mirror to look at Jude's dad in surprise. Jude was kind of shocked, too. It wasn't every day that Dad let any of the younger Winchesters spend time alone with a monster. But since this was Clare's dad, maybe it was meant as a courtesy. Clarence glanced around at everyone else for a second and they all gave him comforting looks as he made his decision.

“Yeah,” he finally said, “as long as Jude can come in with me.”

Jude gulped as he felt his fiance's hand squeeze his own a little tighter. Reluctance and a touch of dread came over Papa's face, but Dad seemed a little more understanding. He weighed the idea in his head for a second before relenting.

“Fine. We'll keep a close eye on you from the window. If he tries to do anything, the rest of us will come storming in. Okay?” Dad settled.

Clare acknowledged the terms with a nod and turned toward the door that led to the next room. Jude's Papa was the person standing closest to it, and though he was still wearing an anxious expression, he slowly reached out to turn the knob and open the door for the two younger men. Jude tightened his hand around Clare's as the warlock's singing faded out.

“Oh, are you back again already? Come to kill me, yet?” the warlock asked, probably toward Papa, “I wish you angels would understand. I have no quarrel with heaven. It's those filthy, lying, twisted, monstrous pack of hounds that call themselves demons that I -”

When Clarence and Jude entered the room and the door shut behind them, the warlock's sentence abruptly halted. Clare and the warlock had locked eyes and now they were just silently staring at each other; Clare with a touch of anger and Caldwell with absolute surprise. As Jude stood next to his fiance, he couldn't help but feel like the warlock knew who Clarence was. Did he know that Clare was his son? Or was he just freaked out that someone else could look so much like him? The disturbing silence seemed to drag on for several minutes as Caldwell studied Clare's face from his seat.

“So... This is it,” he eventually muttered, barely audible, “I always knew that letting Meg live was the right choice...”

Jude gulped. So the guy _did_ know that Clare was his son. If Clarence was upset by that statement, he hid it very well. Jude couldn't tell how his fiance was feeling at the moment. He only knew that Clare had a death grip on his hand.

“Why did you knock her up and abandon her?” Clare blurted.

Jude felt his own face fill with heat. Wow, that was a very blunt and powerful question to ask so quickly. But, then again, Clare had probably wanted to know the answer to that question for a long time... A lighter tone spread across the warlock's face and he almost smiled at Clare.

“I'd hoped that you'd be a boy,” he admitted, his voice warmer than before, even though he ignored Clare's question, “Not that it matters much. It's just, I know first hand how the world treats women with such bias cruelty. Being male has its privileges. Plus, I always pictured how handsome you would be with our mixed genetics. I must say, you look better than I ever imagined -”

“Answer. The damn. Question.” Clarence suddenly barked between clinched teeth.

Caldwell seemed kind of disappointed by Clarence's anger. Did he really expect Clare to be happy to see him? After everything he had been through? The warlock readjusted himself on the chair in the middle of the sigil and stared up at Clarence with a harbored look of innocence.

“I _am_ glad to finally meet you,” he nodded, smiling again, “and I know you have questions, so I'll make you a deal... You tell me about your life first, and then I'll tell you all about mine. And I'll answer anything you ask.”

Jude felt a little uneasy as he stood next to his pale fiance. The man sitting in front of them had done horrible things; raped demons, killed people, tried to kill uncle Crowley... and yet, he seemed so very interested in getting to know Clarence. It seemed like he genuinely wanted to hear Clare's life story. The weird shift in his demeanor was making red flags pop up everywhere for Jude. Luckily, Clare seemed to think the same thing because he was hesitant to reply. But after a few minutes of hard staring, the demon sighed in defeat.

“Fine,” Clare barked, “Let's start with the day my mother carved me out of her womb and tossed me over a bridge.”

The smile on Caldwell's face vanished in an instant.

“... What?” the warlock breathed.

“Yeah,” Clare nodded, his eyes large and voice cold with honesty, “After you left her pregnant and doped up on the side of the road, she cut me out, stuffed me in a jacket, and threw me into the Chicago River. I was lucky a coven of witches found me and took me in,” Clare spat, his voice gradually getting louder and harsher, “Oh, but that didn't last long, because they all _burned to death_ in a house fire that happened when I was eight. I was orphaned for the _second time_ and left alone to defend myself on the streets. No home. No family. God, I was only _eight_! You can't even imagine the things I had to do to survive out there!”

Caldwell was clearly distressed by what he was hearing, and it only seemed to fuel Clare's rage.

“And how do you think I found out about my own birth?” he continued, nearly shouting at the man in the chair, “Because I tracked down my mother. _This_ family of hunters helped me find her. I waited my _whole damn life_ to get to that woman, and when I finally did, she told me that some _asshole_ raped her and left her to die. She never wanted me. She was forced to have me. I was a parasite. I was a _mistake_ -”

Hearing Clarence say those awful things made Jude feel so terrible that he reached out and wrapped his arms around him. Jude couldn't stand it when Clare called himself such horrible things. Luckily, Jude's gentle touch was enough to bring Clarence's anger back down to an acceptable level. Without looking away from the warlock, the demon swallowed a gulp and took a few breaths.

“... Because of _you_ ,” he finished, his voice lower and more accusing, “All of this pain could have been avoided if you would have just kept your dick in your pants instead of putting it in women who never wanted it. You rape them and kill them, but why didn't you kill her? Why didn't you kill me? And how the hell are _you_ even alive? Crowley told me he killed you. We're all supposed to be dead...”

That last line made another ache echo through Jude's heart. His arms tightened around Clare's slender torso as he pecked a tiny kiss to his shoulder. Jude had no idea why Clarence actually told the warlock the truth. Maybe he hoped that if he was authentic, Caldwell would be too. Jude lifted his head from Clare's shoulder to steal a peek at the man seated in the middle of the room – and found that his maroon eyes were actually _glistening_. It seemed like Clare's story cut the warlock to the core, and Jude was surprised. Maybe he thought that Clare had a great life or something.

For a minute, the room was quiet. Clare stood still and let Jude hold him, while the warlock glanced around sadly. It seemed like he was preparing his own speech in his mind; figuring out what to say and the best way to say it. He eventually sat up straight and slowly brought his sight back to Clare's face.

“I'm sorry to hear that,” he offered, as if his apology made any difference, “but it might please you to know that my own life started out in the same fashion...”

Jude glanced over to see Clare's expression. His pained, lovely greenish-brown eyes were narrowed into slits, but he didn't say anything. He waited for the warlock to continue.

“It was many, _many_ years ago. On a tiny farm in Ireland,” he admitted, looking away to concentrate, “My mother and father labored in the fields, herded the livestock, fetched water daily. And when I came along, I was put to work as soon as I could walk,” his voice lowered as he shook his head, “I knew some part of them despised me because I was another mouth to feed. And it got even harder when the ground stopped giving us crops. With less and less food, sheep slowly dying off, and disease setting in, my parents were getting desperate... So, they went to a crossroads and summoned a demon.”

A grimace flickered on Caldwell's face, as if he hated mentioning it.

“I was there, watching from behind a tree. It was a female demon. Beautiful, but deceptive. In exchange for my parents' souls, she promised them a comfortable life of wealth and prosperity. They sealed the deal with a kiss. For a little while, things turned around. Our crops blossomed, our livestock tripled, and my mother even became pregnant with another baby. The demon kept her promise to give my parents wealth and prosperity – but it only lasted a few weeks. Nearly a month after they made that deal, a giant storm came off the coast and demolished our farm. My parents were killed, their souls sent straight to Hell. And I was orphaned. Alone, on a wasted farm...”

As the warlock paused to collect himself, Jude looked to Clare again. The demon's eyes were still narrowed, but he listened, waiting to hear the rest of the story.

“Needless to say, I was outraged and vengeful,” Caldwell picked back up, “I went seeking a way to kill that demon responsible for ruining my parents' lives. Eventually, I found a witch in Scotland. Lovely red-haired lass who taught me a few things in magic. But when I told her about my plan to kill that demonic whore, she ended the lessons. I don't much blame her. Everyone's assigned to their own destiny. Still, her absence left me with quite the conundrum. Who could possibly aid me in my quest for vengeance? That's when a brilliant idea came to mind. In order to ensure someone's demise, you must first go to the source... So, I spoke with Death himself.”

Jude's mouth fell open. Death? The warlock spoke to... death? But how was that possible? Was death an actual person or something?

“I made a deal with him. But Death is not like demon-kind, no. Not in the slightest,” Caldwell explained, “I was able to bargain with him. In exchange for the deaths of demons, he promised to grant me extra lives. For each demon I kill, another life gets added to my own 'dead-line'. Death is a very mysterious creature, you see, and he takes his work quite seriously. Heaven, Hell, he has no preference. Because in time, everything will die. But with my help, Hell will die faster...” he smiled, “So, with Death's blessing and a small piece of his power, he practically handed that demon to me on a golden platter. And let me tell you, she suffered greatly by my hand. See this scar?” he said, pointing to the long pink line that ran down his face, “A souvenir from our time together. She practically begged me to kill her before I was through...”

Jude felt like his skin was crawling. That demon lady may have given those people a bad deal, but did she deserve the torture Caldwell gave her?

“Now, I've tasked myself with thinning out the demon legion until there is nothing left of them,” the warlock concluded, “I punish and end their lives as much as I can -”

“But you rape them,” Clare interrupted, his voice hollow, “What the hell gives you the right to _rape_ them?”

Caldwell sighed and looked away, seeming a little shameful.

“I'll admit, eternity gets lonely at times,” he mumbled, “The desire for intimacy becomes too great and I can't help but flesh out my fantasies... But isn't it better that I perform those acts on demons rather than innocent humans? Do demons not earn their place among the tortured rabble?”

Clare's eyes suddenly flashed black.

“ _I'm_ a demon,” he reminded in a cold, hellish tone.

Pain seeped into Caldwell's face and he nodded slowly. A few extra moments of silence followed, in which he tilted his head toward a far wall and stared at it lovingly.

“Yes. And that's my fault... because I fell in love with your mother,” he breathed.

For the first time since they stepped inside the room, Clare's face released its hard stare. He was suddenly blinking at the warlock with surprise and a hint of caution in his forest eyes. Jude was shocked, too. Caldwell actually loved Meg?

“The other demons I've had in my time were such fighters. Always kicking, biting, screaming, clawing like animals. That's why I started to use opium on them. To calm them down... But Meg... She didn't fight,” he explained quietly, “Whenever she stirred from that heavy sleep, she only stared at me. Blinking. Such beautiful green eyes. It was as though she thought she _deserved_ the pain she was receiving. Looking at her made me start to question my own actions. Made me imagine what life could be like if I only stopped my crusade and spent my time with her... I kept Meg longer than any other demon that fell under my possession, because... She became pregnant...”

At this point, Jude could see moisture building in Clare's pretty green eyes. He was obviously being affected by everything he was hearing. When Caldwell turned back to look at him, a smile rose on his face.

“When I realized she was with child – with _my_ child – I wasn't quite sure what to do,” he said, shrugging a bit, “If she had been any other demon, she would have been long dead. But I couldn't bring myself to harm her, let alone kill her. I kept her under the effects of opium for many months, trying to decide what to do. I knew that if I brought her out of that stupor, she wouldn't stay with me. After everything I'd done to her, she would probably be outraged... But maybe, if I left her alone – if I let her go and live a full life with the child we made – I could see her again some day under different circumstances. Perhaps she would even be grateful for the gift I gave her...”

Clare gulped and the motion caused a tear to sip from his unblinking eyes. Jude watched it paint a wet line down his cheek. Caldwell's smile faded and he shook his head.

“I'm so very sorry that things didn't turn out that way... My son...” he carefully added, “If I had known that she was going to abandon you, I would have went back for you. I would have cared for you myself. You have the same thorny beauty and conviction as your mother, and you would have made a fine apprentice. I would have been honored to raise you... Tell me, what's your name?”

Jude looked to his fiance, who had been frozen beside him this whole time. At first, it seemed like Clarence wasn't going to answer. He appeared too shaken up and confused, and Jude understood why. Finding out that his father wanted him even though his mother didn't must have been difficult to hear. Clare chewed on his lip for a second before speaking.

“Clarence,” he uttered under his breath.

Caldwell's smile returned.

“Ah. Clarence. A fitting name. It means 'bright' or 'clear'. Did you know that?” he hummed.

Clare shook his head once. For a second, he seemed pleased to be speaking so freely to his father. But then, a touch of anger seeped back into his features; as if he was waking himself up from a fantasy to focus on reality. He raised his head a bit higher and cleared his throat.

“Break the curse you put on Crowley,” he demanded.

Caldwell sighed and sat back in his seat, crossing his arms and shaking his head.

“That blasted old fool,” he murmured, “He should have never started this... I'm afraid I can't do that, Clarence. Death himself made the blade I stabbed that demon with. It's his curse, not mine.”

Jude's heart plummeted. What? It was Death's curse? Then how were they supposed to break it? How were they going to save Crowley before it was too late?! Clare finally turned to look at Jude for the first time since they entered the room, and the two young men shared the same look of dread. Looking into Jude's eyes must have made Clarence aware of how much time they'd spent talking to the warlock, because he suddenly wanted to leave.

“Then we'll just make _him_ break it,” Clare concluded, starting to pull Jude toward the door, “Thanks for the tip.”

“Wait,” Caldwell breathed, “I – I have so much I want to talk to you about -”

“I don't want to hear it,” Clare said over his shoulder.

Just as Clare stepped over the threshold, something grabbed onto Jude's free hand. The angel gasped and turned around to see that Caldwell had reached as far as he could inside the trap to grab Jude's hand, keeping the boys in the room.

“Clarence, please!” the warlock begged, tugging on Jude and making him stumble back, “Tell me about this angel. Is he your brother? Friend?”

“Let me go!” Jude barked, trying to get his hand back.

“Please, tell me,” the warlock went on, ignoring Jude to focus on Clare, “I want to get to know you.”

A gust of wind flew through the room, rustling everyone's hair and clothing. Papa had flown inside and aimed a glowing hand toward the warlock.

“Let go of my son. Now,” he demanded.

“Oh, piss off! The boy's fine!” Caldwell shouted, though Jude's fingers were starting to hurt, “Clarence, I -”

Before the warlock could even finish his sentence, Papa lit up the room with a blast of grace. Jude gasped and shielded his own eyes, feeling Caldwell finally let go of his hand. It was a fast flash of light that was gone in seconds, but it left everyone momentarily stunned. When Jude felt safe enough to raise his head, he saw that Papa had lowered his hand – and the warlock was slumped over in his seat with burned out eyes.

“H – holy shit!” Clare breathed, “What the hell did you just do?!”

“I smote him,” Papa calmly admitted.

“Wh – _why_?!” Clare groaned angrily.

“We got the information we needed from him. Besides, he deserved to have the life burned out of him after everything he's done. And he made the grave mistake of touching my child,” Papa sternly noted.

“Cas, that was a bit premature,” Jude's dad called from the other room.

“Not to mention graphic!” uncle Gabe added.

“Well, according to the warlock, Death will give him another life. So I saw no harm in ending this one. And perhaps a few more,” Papa defended.

“Looks like you're right,” Sam said, leaning into the door to point inside.

Jude joined Clarence and his Papa in looking toward the middle of the room – where Caldwell's slumped body was gone. The chair was empty now, sitting crookedly on the sigil. Jude blinked at it in shock. He was gone, just like that! And if he was telling the truth about being constantly revived by Death, maybe everything else he said was true, too...

“Now what?” Jessie's voice echoed from the other room.

Jude's Dad walked into the room, looked at Papa, and sighed as he put his hands on his hips.

“Does anybody have Death's phone number?” he asked blandly.

 

**Notes for the Chapter:**

> And so it was, that Clarence met his biological father for the first time. ;) Yeah, I know. Caldwell is an... interesting person, to say the least. I can't tell you much more about him at the moment, sorry to say. But this bizarre plot will make more sense as it goes on. (I hope. Lol) :) Yes, Death will be making his way into this story, too! (We've got all kinds of guests this time, huh? Lol) I hope that you all enjoyed the tense interaction between Clare and the warlock. I would love to hear about your reactions to his story and his feelings toward Clare! :) Thank you guys so much for reading and reviewing, and I hope you're enjoying everything so far! :) Next week's chapter will be out soon! :)


	7. Chapter 7

With the warlock gone, and a heap of new – and pretty disturbing – information to process, Dean was at a loss. Not only was Clarence's father suspiciously happy to see his son, but he told them that damn curse on Crowley wasn't even his. It belonged to _Death_. Who the hell in their right mind would make a deal with Death? And why would Death be so willing to give extra lives to someone with such evil intentions? To be fair, Dean had only spoken to Death once, and that was well over twenty-five years prior to this mess. But he thought that Death was a pretty chill guy; or spirit or whatever. He didn't seem like the type that would hand out deals like a crossroads demon, but maybe Dean was wrong. There was only one way they were going to find out for sure... and that was to talk to Death directly.

But before diving into a risky plan to summon Death, Dean wanted to talk with his family and make sure they were okay. Especially Jude, Clarence, and Crowley. Jude and Clare were obviously shaken up by everything the warlock said; all those overly-caring phrases. Dean was skeptical about how sincere Clare's dad really was, but there was no way to test the theory that he might be lying, because he was gone now. Plus, Dean had no clue how much worse Crowley's wound was. Time was running out fast and they needed to focus on one thing at a time. So, after rallying everyone together in the dungeon, Dean requested that Cas and Gabe fly everyone back to Bobby's house. All four adults, all four kids, and Gabe's dog showed back up in the salvage yard in seconds. Jessica, Oliver, and Gabriel almost immediately headed inside, but Dean and the rest lingered back.

It seemed like Clarence was having a pretty tough go of this. His head was down and his eyes were vacant, as if he was numb to the rest of the world around him, even though Jude was still clinging to his hand. And because of the flight, Jude was holding onto Cas's arm with his other hand; face buried into his Papa's trench coat as if he was trying to keep himself from throwing up. Cas pet the back of Jude's head comfortingly, but his eyes were on Dean. The angel was giving him one of those ' _what should we do, now?_ ' looks. And Dean knew that the first thing he needed to do was talk the boys down.

“Hey,” he began, reaching out to pat Clare's shoulder, “You gonna be alright, kid?”

Dean was giving Clarence a chance to say whatever was on his mind; a chance to let other people know exactly how he was feeling. But maybe _he_ didn't even know how he was feeling, because he nodded and shrugged it off.

“We've gotta save Crowley,” he muttered blandly, shifting the attention back to the big picture.

Dean shared another look with his angelic husband, who seemed equally concerned for the demon and their son. There wasn't much else they could do for the boys other than be there for them.

“That's right,” Dean agreed, turning to Sam and nodding toward the back door, “I think we should talk to Bobby. See what he thinks about this Death thing...”

Sam silently agreed and led the way into the house. What had been a chaotic scene a few hours before was now quiet and somber. In the study, Rowena and Bobby were working at a steady pace; transferring soaked bandages back and forth from Crowley's abdomen. Crowley himself was frozen in a wincing position, with his arm and fist braced over his eyes and his teeth clinched. Even from the kitchen, Dean could tell that the black markings had stretched further across his body. The demon's entire stomach was dark and painful looking, inching up his chest and nearly reaching his throat. Damn, the curse was fast. If they didn't do something soon, Crowley was going to be in real trouble...

“Clare,” Dean heard Jude's timid voice whisper behind him, “Do you want to talk about -?”

Before Jude could even finish his sentence, Clarence was stepping away from the group and entering the study to kneel down next to Rowena and Crowley. The guy clearly didn't want to talk about anything that was happening, even to Jude. Dean turned around to give his son a half hug along with Cas.

“It's alright, buddy. Clare just needs some time,” he reminded as kindly as he could, “Why don't you just keep him company until he's ready to talk?”

Jude nodded at his father's suggestion and slowly ventured into the study to help Rowena and Clare with Crowley's herbal medicine. In the meantime, Bobby took the opportunity to step away and meet the other Winchesters in the kitchen.

“What the hell happened? Why ain't the curse broke yet?” he asked in a hurry, voice anxious and a bit heated.

Luckily, Cas, Sam, and Gabriel were all standing near Dean and helped him deliver the bad news to their worried uncle.

“The curse wasn't made by the warlock. It was made by Death,” Sam explained.

“And the reason the warlock is still alive is because Death resurrects him every time he dies. Some kind of stupid deal they made about killing demons. He and Death are total Frat bros or something,” Gabe sighed.

“The warlock is also gone. Because he vanished after I smote him,” Cas admitted boldly.

Bobby blinked between all four men in his kitchen, his aged face growing pale under his faded blue hat.

“Death?” he repeated, shaking his head, “How the hell are we supposed to get Death to break a curse?”

“Find him and ask him nicely?” Gabriel mumbled sarcastically.

“That rests on the possibility of us actually finding him and getting him to speak with us, first,” Cas pointed out.

“We could summon him. We've done it before,” Sam reminded, “Look, we're going to have to do something. We need to come up with a plan fast. I mean, Crowley doesn't have much time, guys.”

“Sam's right. I'm done waitin'. I ain't sittin' here and watchin' Crowley suffer anymore,” Bobby denied, voice tainted with pain, “Y'all remember how to call him in?”

“I know how to do it,” Cas assured, stepping forward, “However, I don't think that this house is a suitable place to summon Death itself. I suggest we stage this encounter elsewhere.”

“Fine with me. What place you fellas got in mind?” Bobby asked, glancing around.

A moment of silence followed, in which everyone pondered a meeting place. If there was one thing Dean knew about Death, it was that he loved to eat. Deep dish pizza and pickle chips were among his favorite things. At least, from what Dean could remember. And if Death was drawn to good eats, he knew a few places that would serve the purpose. Maybe even one close by.

“I've got an idea,” Dean quietly mentioned.

* * *

Gabriel narrowed his eyes at the yellow neon sign glowing in the window above his head. The words flashing in bright colors were so hilarious that he didn't know whether to laugh hysterically or cry from the perfection.

“Frank Johnson's World Famous Wienies?” he read aloud, eyes falling to the smaller words underneath, “A delicious meaty flavor in every mouthful? …Oh my Dad, Dean-o. I knew you liked meat-swords, but wow, not to _this_ extent. You just _adore_ having a wiener in your mouth, don't you?”

“Zip it, shorty,” Dean hissed, tossing Gabe a glare, “I only ate here once, okay? But they've got this thing called the 'Kansas City Baseball Bat', which is basically just a deep-fried, bacon-wrapped Twinkie on a stick that -”

Gabriel didn't even hear the rest of Dean's sentence because he was too busy laughing. Holy shit! Could these puns and innuendos be anymore obvious?! This place should just change its slogan to 'We love dick almost as much as you do. Come eat with us.' Gabe had to reach over and hold onto his husband's arm just to stay standing as he doubled over with laughter. But Sam, for some reason, didn't find it as funny as Gabe did.

“Okay, Gabe. We get it. It's funny,” Sam grumbled, pulling Gabe back to an upright position, “Now, can you please focus? Crowley's life is at stake.”

Gabe giggled a few more times – having seen that the diner mascot was a smiling, waving hotdog pouring mustard on itself – before coughing and trying to settle down. Sam was right. The poor ol' king of Hell was all dinged up and only getting worse, and they really needed to get the guy some help.

“Alright. I'll try my best. Scout's honor,” Gabe offered, even raising up the three fingers as a promise.

The rest of the guys – Sam, Dean, Cas, and old man Singer – tore their annoyed looks away from Gabriel and placed them back on the diner ahead. The place was empty, due to it being after hours, and only the neon sign was on. All the other lights were out, which was a good thing. That meant the Winchesters would be able to sneak in and summon Death no problem. And if Death had a thing for puns and hotdogs, this would be an even easier piece of cake.

Castiel led the way inside by casually breaking through the flimsy lock and turning on a few lights with his grace. Bobby and Sam made themselves useful by moving a few tables out of the way while Dean headed back into the kitchen; probably to see if he could find one of those deep-fried Twinkies. In the meantime, Gabe assisted his little bro with gathering all the ingredients necessary to summon the dust bowl that was Death.

“I hope you know what you're doing, Cassie,” Gabe muttered to the seraph while the two of them were alone, “The bag of bones you're about to call has the power to reap us too.”

“I'm aware,” Cas replied, “but I will do whatever it takes to see that our family remains intact.”

Gabe smiled fondly at his sibling as he slid a sacrificial bowl in front of him. There was something so admirable about the way Cas said and did things. He was always so sincere and to the point; so prepared to do the right thing no matter how difficult. Though he was too embarrassed to admit it, Gabriel often wished that he could be more like his rebellious, blue-eyed little brother...

Dean eventually made it back from the kitchen, carrying a plate full of 'Kansas City Baseball Bats' and a few other treats, including what looked to be cheese balls, banana chips, and chocolate eclairs. He carefully positioned the plate full of goodies on the counter next to Cas's bowl, as if he was hoping that the food would be the first thing Death saw. With their edible peace offering ready, Cas paused to share a confident look with Dean before filling the bowl with blood and saying a Latin phrase.

Gabriel could tell that Castiel altered some of the words, though. Instead of summoning and binding Death, Cas was simply calling him to join them at the diner. More of a request than a forced summons. The rest of the guys waited and searched around the inside of the building, looking to see where Death might decide to pop up. It had been a long time since Gabe had seen the old bastard – a few hundred-thousand years, at least – so he wasn't sure what to expect. From what Gabe remembered, Death was like one of those old men who always hated when kids were on his lawn – but instead of yelling at them to get off, he just killed them. Dude had a killing fetish ten miles long.

But as he stood between to his little brother and tall husband, Gabriel felt a shift in the air. It grew colder, calmer, and somehow a little more difficult to breathe. There was no denying that a strong presence had appeared in the diner with them. Gabe looked up to see Sam whip his head toward the left and he followed the kid's line of sight toward the entrance. The glass door of the diner was standing open and there was a shadowed figure standing in the doorway. It was tall, slender, and holding a walking cane. The hem of the figure's long coat was eerily still, as if the person wasn't even breathing or moving. It looked like some kind of prop for Halloween and it gave Gabriel chills. Holy shit. Was Death always this freaking creepy?

For a second, everybody just stood there and gazed cautiously at the unmoving figure. Nobody said a word for a long time and it was really starting to get on Gabe's nerves. What was with all this ridiculous tension? They were here to talk, not have a staring contest.

“Well. I guess the 'death' of the party has arrived,” Gabriel whispered toward his husband, trying to break through the weird vibe in the room.

“Gabriel,” an icy British voice murmured from the doorway, “God has made many things, but you are perhaps his most annoying, ill mannered, childish creation. If at all possible, I would like you to refrain from attempting anymore jokes for the duration of this meeting. Otherwise, you should not speak at all. Are we clear?”

Gabe's jaw nearly hit the floor. Whoa! What the hell?! Who the hell did he think he was talking to?! The archangel felt the urge to roll up his sleeves, stomp toward that bastard, and give him a piece of his mind. But then, he felt the distinct grip of Sam's big hand on his wrist. There was a very real sense of dread in Sam's eyes, as if he was terrified of Death and what he might do if Gabe tried anything stupid. To console his worried moose, Gabriel closed his mouth and gave Death a hateful glare instead. The figure in the doorway nodded once.

“Good,” the accented tone confirmed before turning toward the others, “I assume there's a perfectly sound reason you asked me to come here. Other than to share a meal.”

A boney finger jutted out into the light to point toward the plate of food on the counter. Dean immediately reached over to twist the plate around invitingly.

“Uh, ac – actually, this is just a gift,” he offered nervously, “We, um, just wanted to ask you a few questions while you eat. If that's okay...”

Everyone stared at Death's shadowy form afterward, waiting to see what his reaction would be. At first, he didn't even move. He only stood there in the dark, observing the group like some kind of creepy mannequin. Eventually, Death stepped slowly into the room and into the light, revealing his long nose, large forehead, and thin, down-turned lips. The guy looked more like a ghost than a horseman. His steps echoed around the silent diner as he made his way over to the counter to look at the plate Dean made him. He scanned all the items on it before slowly sliding onto the stool at the counter. He propped his cane against the wood, picked up a banana chip, and gingerly slid it into his mouth.

“You have five minutes,” he mumbled between his crunches, “Make them count.”

“We need you to break a curse,” Singer jutted over to practically beg, his voice shifting higher when Death's eyes fell to him, “Uh, please. Your honor.”

“What curse?” he muttered blandly as he picked up the eclair to take a bite.

“The one you put on the blade that you gave to a warlock named Caldwell,” Dean explained.

Death paused to swallow his bite and delicately dab the edges of his mouth with a napkin.

“Ah. Caldwell. The demon killer,” he recited, his eyes traveling to Dean as he shook his head, “I never gave him a blade.”

Gabriel glanced around at the rest of the guys, seeing equal amounts of confusion. What? Death never gave the warlock the blade? Obviously, one of them was lying. And Gabe was more inclined to believe Death over a rapist demon killer. At least Death was honest, right?

“Well, he stabbed my husband with a cursed blade and said that you made it,” Bobby spat.

“Then he has spun you a fascinating tale,” Death concluded, “Will that be all?”

“No, wait,” Dean said, “He said that he made a deal with you. That for every demon he kills, you give him an extra life. Is that true?”

Death paused again to bite into one of the cheese balls, but nodded his head.

“That one _is_ true,” he agreed.

“Why?” Cas blurted, his eyes narrowed and head tilted, “Why would you make that kind of deal with him?”

“I see no need to explain my actions to the likes of bacterium such as yourself, but if it means speeding up five minutes...” Death sighed, “I don't make deals often. But when he came to me and offered to kill as many demons as he could get his grubby paws on, I simply couldn't turn him away. I'm extremely old and my... job... is slowly losing its luster. If a worthless being wants to help me further the end of a race, so be it. I assume he cursed a blade to make things easier for himself.”

“But if that curse belongs to him, how are we supposed to make him break it?” Dean asked, “We can't exactly threaten his life if you're just going to give him another one.”

“An astute observation,” Death nodded, sitting his 'baseball bat' down and moving to get up, “but also not my problem. The Twinkie was a bit overdone, Dean. Next time, gift me with something a little less greasy, hmm?”

Death turned to leave, but Dean instantly rounded the counter to jump in front of him, holding both hands up.

“Wait!” he almost shouted, “Look, man, we've gotta do something about this. If you can't break the curse, then why don't you just break your deal with the warlock? That way, we can kill him permanently if -”

“He's doing a relatively fine job of killing demons. I see no need to end my contract with him,” Death argued.

“Then make a new deal. With us,” Dean blurted, “If you want dead monsters, we'll give you dead monsters. Sam and I have taken down hundreds of them.”

Death paused to study Dean's face, and his sunken eyes twinkled a little bit. It gave Gabriel the chills.

“That's a tempting offer...” he croaked in a whisper, “Very well. You want to make a deal?”

“Yeah. What do you want us to do?” Dean asked.

“I want the soul of a Winchester,” Death stated.

Every other person in the room nearly gasped in unison. What? Death wanted one of their souls? Which one of them?! And _why_?!

“ _Wh – what_?” Dean breathed.

“Yes,” Death nodded, “If you wish for me to end my contract with Caldwell, I want one of your souls as compensation. Sam or Dean. The choice is yours.”

All of the guys in the room looked between the two hunters in horror. That bastard wanted either Sam or Dean?! Hell no! He couldn't have either one of them! _Especially_ not Sammy! Gabriel wrapped his entire arm around his husband's lengthy torso for good measure, daring anyone to take him away.

“Why?” Dean barked, eyes narrowed suspiciously.

“You and Sam kill hundreds of monsters. You said so yourself. But you see, if you _hadn't_ killed those monsters, they would have killed _thousands_ of people. Maybe even millions,” Death pointed out, “Demons, angels, humans – I don't care which race dies out first. I just want this job to be over with as quickly as possible. And you hunters are slowing the process to a mere crawl. I'm tired of waiting. You want that curse broken and warlock dead? Fine. But the cost is a Winchester's soul.”

The diner went absolutely silent for an entire minute. All of the people in the room glanced at each other with varying expressions, all wondering the same thing. How could Death ask them to do such a thing? They couldn't give Sam or Dean's soul away like that! The guy was out of his mind! How could he back them into a corner like that?! After seeing that no one else was going to say anything, Death placed both of his hands on his cane and blinked at Dean.

“I'll give you time to think about it,” he offered, “Call me when you've made your decision.”

And the guy was gone.

Gabriel barely comprehended that Death had left the room because he was too preoccupied with the feeling of Sam's body breathing in and out inside his arm. Sam's heart was beating, his lungs were working, and Gabriel couldn't even begin to imagine what he would do if he had to give that away. Sam couldn't die. His soul couldn't be given to Death. It just couldn't. _Gabe would never allow it_. 

“It's me.”

Gabriel's heart leaped into his throat at the sound of Sam's voice. The archangel turned to the side to fully look up at his husband, who seemed weary and sad, but fully committed.

“I'll do it. I'll go,” Sam sighed, “I've lived a good life and I -”

Sam didn't get to finish his sentence – because Gabriel reared back and slapped the piss out of him. Sam groaned and held his reddened cheek, nearly glaring down at the archangel who hit him.

“Ow!” he grumbled.

“ _Don't you ever say that again, you giant beautiful prick!_ ” Gabe shouted, feeling tears rise in his own eyes, “You are not some chess piece for Death to play with, okay?! You are _my husband_! You are _Jessica's father_! And you are _not_ going to sacrifice yourself for anyone else ever again, do you hear me?! Stop trying to be a martyr! Stop being such a selfless moose! _Stop breaking my heart, dammit_!” 

After Gabriel croaked the last sentence with a broken voice, he threw himself at Sam; burying himself into the chest cavity of the person he loved most in the world. Sam's musk alone was able to make the moisture escape his eyes. Though his words – and violent actions – were a bit extreme, Sam still found it in him to hug Gabriel back. His long arms circled the archangel and Gabe had to hold in a sob. See? Sam didn't really want to give his soul away, either.

“Gabe's right. You're not doing it,” Dean agreed, “... I am.”

“No, you most certainly are not, Dean,” Castiel immediately rebutted, flashing closer to him with a fierce look in his eye, “Jude, our family – everyone needs you. And I need you more than anyone.”

“What else are we supposed to do, Cas? Huh? Let Crowley die?” Dean snapped.

A sharp inhale came from Bobby's side of the room and everyone else glanced over to see that he had hidden his face with the bill of his hat. He was looking down at the floor, but Gabe could tell that he was holding back tears because of the way his bottom lip was quivering.

“I... I was thinking of that,” he mumbled, voice high pitched and full of grief, “I don't want the ol' bastard to go... but I know he wouldn't want any of you to trade places with him, either... If somebody's got to die, Crowley will offer to be the one to go. I know he will... I just... I hate seein' him go that way...”

Somber silence settled in the room again as everyone listened to Singer's pitiful sniffles. Gabriel hated this stupid situation. None of them deserved to die. Together, the Winchester family had saved countless people! The whole world, even! If anyone deserved to die, it was the prick who thought he could tear them apart with a deal... Gabriel blinked away his own tears and stood up straight, slowly letting go of Sam as a brilliant idea formed in his head. Of course! Why hadn't he thought of that before? It was so obvious!

“Wait a minute. None of us have to go,” he breathed, looking around at the rest of his family.

Of course, they all gave him confused and annoyed looks, but he expected that.

“Isn't it obvious?” he asked, feeling a smile grow on his face, “We just have to kill Death.”

Bobby tilted his head and Dean rolled his eyes with a groan, both in disbelieve that Gabriel could suggest something so bizarre.

“I'm serious,” Gabriel continued, “If we kill him, his deal with the warlock will end. And if the warlock can't come back to life, we can kill him too. And then Crowley's curse will be broken and his workforce will be safe. See? It's a win-win-win!”

“He's right,” Bobby said, finally looking up again, “Crowley told me all about contracts. If one party's dead, the contract is void. Especially ones bound with blood magic or a ritual.”

“But we're not talking about some random guy, here. We're talking about Death,” Sam breathed, sounding bewildered, “ _The_ Death. We can't just kill Death!”

“Actually, we can,” Castiel argued with a nod, “Death has a weapon – a powerful scythe – that will reap any being in the universe, even our Father. If we were to acquire it and use it on him, we may be able to end his life.”

Dean sighed dramatically and rubbed his own forehead.

“Wait. Let me get this right,” he grumbled, “Not only are you suggesting that we kill Death, but that we kill him with his own damn weapon?”

Castiel nodded to his husband, his face void of humor. Gabriel, on the other hand, was smiling brightly. He felt like he had just solved the world's most difficult and heart-wrenching puzzle. For a moment, Dean seemed completely at a loss. He only shook his head and tossed his hands in the air, as if he couldn't believe that he was even hearing this crazy plan. But he eventually bit his lip and swallowed a huge gulp.

“Then I guess we're gonna kill Death with his own damn weapon,” he groaned, “But if we're gonna attempt this crazy-ass plan, we need to hurry up and get it done. We don't have a lot of time.”

“Agreed,” Singer nodded sagely, his sadness slowly being replaced with hopefulness, “I say we head back to my place and talk to Crowley about it first. He might be able to give us some advice.”

“Evil advice?” Gabriel asked with a wink.

“Probably so. But we're gonna need it,” Bobby finally smiled.

Sam and Gabe stood by while Bobby and Dean grouped around Castiel, all preparing to fly back to Bobby's house.

“I just want everyone to remember that this was not my idea, okay?” Dean said, “So when it inevitably blows up in our faces, I'm not to blame.”

“Take heart, Dean. This plan will not fail,” Cas predicted sweetly.

Dean only gave the seraph a weary look before the three of them – he, Cas, and Bobby – disappeared from the room. Gabriel reached back to take his moose by the arm and fly away with him, but Sam reached up to grab his shoulder instead.

“Wait,” he requested softly.

The large man slowly pulled the archangel closer to him in the diner, so that he could cup Gabe's face with both hands. Gabriel held onto Sam's wrists as he looked up into his large, serious eyes. The kid was tender all of the sudden; loving and careful.

“I'm sorry for scaring you, Gabe,” Sam almost whispered, his low voice calm and honest, “I just wanted to help and I didn't think of you and Jess first.”

Gabriel nodded inside Sam's warm hands, feeling a billion butterflies burst free in his stomach.

“Sorry I slapped you,” Gabe offered in return.

A giant smile flashed on the moose's handsome face, making the butterflies swarm faster in Gabe's belly.

“That's okay,” he nodded, his smile dimming back into seriousness, “I know how much you love me.”

Gabriel gulped, feeling his heart surge.

“You better know,” he breathed in a playfully threatening tone.

Sam smirked back before finally lowering his pretty mouth to Gabe's. Gabriel plunged into the kiss fully, reaching up to tangle his fingers in Sam's long hair and smothering him with tongue. It lasted a few solid seconds before Sam pulled back to grin and reach toward the counter.

“You want to try this 'baseball bat', don't you?” Sam asked, holding up the bacon-wrapped Twinkie on a stick.

“Geez, it's like you're inside my head, moose,” Gabriel chuckled, taking the stick from Sam so that he could chomp a huge bite from the fresh side, “Mmm... Death is an idiot. This shit is amazing.”

The sound of Sam's laughter made Gabe's heart soar. It was his favorite sound in the world, other than their daughter's giggle, and he was glad that he would never have to say goodbye to that sound.

Because they were going to kill Death with his own damn weapon.

 

**Notes for the Chapter:**

> For the record – as you could probably tell by this chapter – I absolutely _hate_ when Sam or Dean willingly sacrifice themselves; as if they don't know their own worth. The show does it waaay too often. And I know that the whole 'selfless hero' motif is admirable and sweet, but come on! It's so needlessly dramatic and heartbreaking! That's why I had Gabriel slap Sammy in this chapter; because I secretly want to do it to the boys every time it happens on the show. Lol. XD (This is probably hypocritical of me, because I'm actually using one of the show's _other_ over-used tactics, which is to have the boys kill their opposition until they accomplish their own desired outcome. But, hey, I say Crowley is worth it. lol) ;D I hope that my interpretation of Death was close to canon. He made this chapter pretty fun to write. And I know that we didn't get to see or hear much of Clare's reaction to his father this time, but it's coming. I promise. :) Thank you guys so much for reading and reviewing! And for putting up with my weirdness. I adore every single one of you! :) The next chapter will be out soon! :)


	8. Chapter 8

After their small, personal moment in the diner, Sam and Gabe flew back to Bobby's house to be with their family. Sam, of course, wanted to be involved in the formulation of the insane plan to kill Death. More than anything, he wanted to hear everyone else's theories because, frankly, he didn't see how it would even be possible. But then again, they had defeated Darkness together. Killing Death wouldn't be much different, would it?

The scene in Bobby's study was about the same as it was when they left. Crowley was still laying on the couch with Rowena, Bobby, Clarence, Jude, and Jessica crowded around him; all transferring bandage after bandage to his blackened stomach. It almost looked like the curse was eating away at his body; causing the tissue to break down and curdle into black goo. The eery coal-colored sickness had finally reached the top of his chest near the base of his neck, and he was lowly huffing painful noises. It was clear that Crowley was in a tremendous amount of pain and it broke Sam's heart. He wished there was more that they could do.

“R – Robert?” Crowley groaned, his eyes clenched shut and hands balled into fists.

“Yeah, darlin', I'm here,” Bobby replied, reaching up to clutch the demon's shoulder.

“N – next time we fight a warlock, remind me to k – kill him before he has a chance to stab me. This is... bloody ridiculous,” Crowley breathed.

Almost everyone else in the room exhaled and smiled, and Sam reached over to give Gabe a half hug. No matter how much pain Crowley was in, he was still himself; he was still fighting to stay alive. And that was enough to give their family hope.

“I'm still a wee bit confused,” Rowena huffed angrily, “Ya've had a chance to talk to Death, yet Fergus is still meltin' away in me hands. What the blazes is going on?!”

“The warlock lied to us,” Cas boldly informed, “Death did not create the curse. The warlock did.”

Sam's eyes instantly darted to Clarence, who had raised his head a bit. It must have been difficult for him to hear that his father had already lied to them once. If he had lied about making the curse, what else had he lied about? Of course, Jude reached over to pat Clare's arm, but the young demon didn't respond. He just went back to dipping some gauze in Rowena's healing mixture on the coffee table.

“So, we're going to kill Death. With his own weapon,” Gabe followed up with confidence, “That way, his deal with the warlock is void, and we can make the warlock break the curse.”

“Kill Death? Have you lot finally gone off the deep end?!” Rowena gasped.

“Maybe,” Dean nodded, “But Crowley's family. It doesn't matter what we have to do, we're not letting him die.”

A loving, somber tone invaded the study after Dean's words. Every person in the room was looking around; scanning the faces of all the people they cared about most, especially the injured demon on the couch. Beneath his cringing pain, Crowley seemed genuinely touched that Dean would speak so highly of him. During their small family moment, Jessica climbed up from the floor and made her way over to her parents.

“Hey, Dad?” she said, reaching up to tug on Sam's jacket sleeve, “Can you go check on Ollie? Rowena sent him out a while ago to get some more supplies out of the garage and he hasn't been back.”

Sam resisted the urge to roll his eyes. Oh boy. Oliver had probably taken a wrong turn or something and ended up lost among the stacks of mangled cars in the salvage yard. Sam reached up to pat his daughter's shoulder, wanting to give her some reassurance.

“Don't worry. I'll find him,” he promised.

“Hurry up, Moose. We've gotta make arrangements for Death's funeral,” Gabe reminded.

“Got it,” Sam mentioned over his shoulder as he headed out the back door.

Sam wasn't exactly sure what time it was at the moment. But judging by the lit streetlights, the moon overhead, and his own exhaustion, he assumed it was at least ten or eleven o'clock at night. He really hoped that Oliver hadn't taken a wrong turn and gotten lost, because with everything else going on, no one could afford a search party. Sam called the kid's name several times and looked around as he made his way toward the garage. The side door was cracked open and light was coming from the inside, so there was a chance Oliver was still looking for whatever Rowena sent him after.

Being careful not to trip over some stray gardening equipment, Sam marched over to the garage and let himself inside. The distinct smell of spray paint was the first thing he noticed, followed by the sound of Oliver's voice speaking. The kid was saying something, but it wasn't English. Intensely curious, Sam quickly rounded some shelves to find Oliver standing near a freshly drawn trap, holding open a book, and trying his best to speak in Latin. Sam almost couldn't believe what he was seeing. That trap on the floor was almost the same as the one they used for the warlock back in the bunker. And that chant Oliver was repeating; it was almost the same they recited earlier. What the hell was Oliver trying to do? Was he – _summoning the warlock again_?!

“Oliver!” Sam shouted.

The red-haired kid stopped short and spun around to see Sam marching toward him, and his face suddenly paled in the fluorescent light.

“What the hell are you doing?!” Sam hissed.

“I – I'm going to trap the wizard guy,” Oliver admitted in a squeaky voice.

“ _No_! You can't do that! Not _here_!” Sam nearly yelled, yanking the book out of the kid's hand, “Crowley is only twenty yards away! Along with Clarence and everyone else! You can't just summon a warlock this close to them!”

“But, if he's trapped in the circle, then he can't get out -”

“Oliver. Listen to me,” Sam barked, grabbing the kid by both shoulders and looking him in the eye, “You are _not_ a hunter. You are barely even an adult. You cannot go around summoning creatures that you don't even know how to fight! Especially not by yourself! What would you do if he actually showed up, huh? Try to fight him with one of Bobby's shovels?!”

“Hmm. That would have been quite entertaining. But still ineffective, I'm afraid...”

Sam gulped at the sound of the calm voice that floated from across the room. He and Oliver stared at each other for a few extra seconds with fear before turning to see the person standing in the garage with them. It was him; Caldwell, the warlock. He was alive again, looking exactly the same as he did earlier when he spoke to Clarence. Death had revived him, just like he said he would. Only this time, he wasn't in a trap. The warlock was casually leaning against one of Bobby's metal shelves, watching Sam and Oliver with a playful smirk. Sam's heart dropped. Shit. Oliver's premature ritual had worked. The kid had summoned the warlock to the garage, but not to the trap...

“My son is just inside, you say?” Caldwell mentioned, gesturing toward the door of the garage and standing up straight, “Thanks for letting me know. Don't worry, folks. I won't be here long.”

“Hey! You can't go! Come back here!” Oliver called.

The red-haired kid reached over and grabbed a brick off a nearby table to hurl it toward the other side of the garage. Sam assumed that Oliver was attempting to hit the wall with it – but the heavy brick found the back of the warlock's head, instead. When the brick bashed the warlock over the skull and he skidded to a stop, Oliver gasped and covered his own mouth; his face turning pale with horror and embarrassment. Sam, too, was filled with dread. They were standing in the same room with a powerfully magical being, and Oliver had broken a brick over his head...

The warlock slowly turned around with a shocked and angered expression, pointing his glaring eyes straight toward them. Sam didn't know what to say or do. He was frozen in place, only able to blink and stand next to his daughter's clueless boyfriend. Without saying a word, the warlock brushed the brick crumbs from his coat and raised his hand. The motion caused a nearby set of jumper cables to lift from the garage wall. The warlock then flicked and twirled his hand, making the cables fly over and wrap themselves around Oliver and Sam. The cords twisted the two of them together, making them face each other in a tight hold. It happened so fast that Sam barely had time to comprehend it was happening.

“Say, that looks like a nicely built portal,” the warlock said, gesturing to the one in the back of the room, “Where does it go? Ah, well. Doesn't matter. You boys have a lovely trip.”

Before Sam could even inhale a breath to pray his husband's name, he and Oliver were suddenly flying through the air. The two of them were tossed into the portal in the back of Bobby's garage, spinning in a tight bundle between the rocks. A vale of darkness covered them as they screamed and fell together in a forced embrace. For a moment, there was nothing but darkness and air, until they finally hit something solid. They 'thumped' hard on the ground, and it shot pain all through Sam's left side.

As soon as he opened his eyes, Sam knew that they were in Hell. The bleak and deadly atmosphere, mixed with distant screams, reminded him as much. Luckily, the jumper cables loosened their grip and Sam was able to untie himself from Oliver. It wasn't until he tried to lift his left side that Sam realized just how much agony he was in. His entire left arm was throbbing, sending waves of pain up to his shoulder. He tenderly gripped it with his right hand and could feel the bump on his forearm. Dammit! Sam's arm was broken! And he was in Hell! With _Oliver_! Ugh, could this get any worse?!

“S – Sam?” Oliver's tiny voice asked in the dark, “Where are we?”

Instead of answering the dumb kid, Sam clenched his teeth to combat the pain and rolled up to stand on his feet. He stumbled over the stray jumper cables on the floor to feel around for the portal – but it wasn't there. The vale they passed through was gone. That meant the warlock had probably smashed the portal after he tossed them inside. Sam shivered a little as he clung loosely to his broken arm. With the portal broken and Crowley unable to teleport, Sam knew that he was stuck there. In Hell. With Oliver Thompson...

“Hell,” Sam breathed, “This is absolute Hell.”

* * *

Jessica huffed a breath as she glanced toward Bobby's backdoor for the twentieth time. She was sure that her dad would have found Ollie by now. What was taking him so long? Was Oliver in trouble or something? How could he have gotten into trouble just from walking out to the garage? All of these unanswered questions were only making Jess feel worse.

“Jude,” Jessica suddenly said, handing off the rest of Rowena's supplies to him, “I'm going to go find Dad and Ollie. I'll be back as soon as possible.”

Jude nodded and took the bandages, silently agreeing to take over her spot until she got back. With everyone else busy helping Rowena – and talking about some kind of crazy idea to kill Death – Jessica made her way quickly through the kitchen and out into the salvage yard. It was dark outside; only lit with the streetlights over head and the faint line of light coming from the garage door that was cracked open. Were they still in the garage? Maybe they got caught up in having a conversation or something. Jessica's heart lifted the tiniest bit when the idea of Oliver asking her father for her hand in marriage came to mind, but she quickly dismissed it. As much as she wished that her dad and boyfriend were discussing a future wedding, she knew that it couldn't be true. Dad and Ollie had never gotten along...

Still, when Jessica got close to the garage, she tried to be as quiet as possible, just in case they were talking. But there was only silence inside. The lack of noise finally led Jess to walk into the room to look for them.

“Dad?” she called, “Ollie?”

Only the distant chirp of crickets from the open door replied. It wasn't until she rounded a few metal shelves that Jessica fully understood what was going on. A freshly painted trap and the Memphis library book from Grandpa John were both on the floor. Beyond that, Bobby's portal – the one that he and Crowley used to cross back and forth from Hell so that they could see each other whenever they wanted – was broken into pieces. The black rocks were scattered and smashed all over the floor, and the vale was gone. Jess's hands slowly rose to cover her open mouth as she looked at the scene in front of her. No! The warlock had been there! He must have broken the portal! Where were Dad and Ollie? Were they – in Hell?!

Horrified by the devastation and the thought of her father and boyfriend being in danger, Jessica turned to run back toward Bobby's house. There was no time to waste. The others needed to know about this immediately.

* * *

“Dammit, Oliver,” Sam groaned as he turned around to glare down at the kid on the floor next to him, “Why do you always have to make things so difficult?”

“ _Me_? _I_ make things difficult?!” Oliver nearly gasped, “If you hadn't barged in and tried to stop me, I would have finished catching the warlock and everyone would have been -”

“ _What_?!” Sam interrupted, feeling fire flare in his own chest as he clung to his broken arm, “Oliver, you didn't even draw the trap correctly! If I hadn't walked in, that warlock would have _killed_ you or worse! And now look! We're stuck here in Hell, all because of your stupid dream to be a hunter!”

“It's not stupid! And it's not a dream!” Oliver yelled back, glaring up from the floor, “I _am_ a hunter!”

“ _No, you're not!_ ” Sam shouted back.

The sound of Sam's loud voice echoed down the corridor, and was followed by low, distant moans and screams of souls being tortured. The realization that they could be heard by other creatures seemed to resonate between Sam and Oliver. They both paused their argument to look around and hope that no one was coming after them. In an effort to make himself less noticeable, Sam backed up against the wall and carefully slid down to sit. The motion accidentally jostled his arm and he had to bite down a yelp. Shit, he could feel the broken bones moving around! Where was Gabriel's healing touch when he needed it?

“G – Gabriel,” Sam suddenly prayed, realizing that his husband might be able to hear him, “If you can hear me, Oliver and I are trapped in Hell. The warlock is back. The portal's broken, and so is my arm... Please get us out of here.”

Hearing Sam pray must have given Oliver the same idea, because the kid lowered his head and started talking too.

“Jess,” he almost whispered, “I'm sorry... I tried to do the right thing...”

Sam couldn't stop the irritated scoff from falling out of his own mouth. He honestly didn't mean to do it so loudly, but of course Oliver heard it and instantly snapped his head up to glare at Sam again.

“It's not funny,” he barked, “I really _am_ trying to do the right thing!”

“No, Oliver. Staying in college to get a good education is the right thing,” Sam hastily explained, sitting up straight to point at him accusingly, “Getting a real job to financially support yourself and your family is the right thing. The _wrong_ thing, is to go out and nearly get yourself killed trying hunt something that you've never even been trained to deal with!”

“ _Hey_! This is _my_ life, okay?!” Oliver shouted, sitting up to match Sam's angered pose, “I'm sick of people thinking they can boss me around and make me do what they want! Mom wants me to be a lawyer, Dad wants me to be a baseball player, my boss wants me to be a veterinarian, you want me to get a 'real' job and stop dating Jessica -”

“What?” Sam blurted, shaking his head, “I never said that!”

“You don't have to say it. I know you hate that we're together,” Oliver spat, narrowing his brown eyes toward Sam in the dark, “Ever since we were kids, you always tried to get between us. When I took her to that dance, you showed up and ruined it -”

“Oh great. Let's dig _that_ skeleton back out of the closet for the millionth time,” Sam groaned.

“Well, you did! You ruined our first dance!” Oliver snapped, “Admit it, Sam! You think that everything I do is wrong, _because you hate me!_ ”

After Oliver delivered his last biting accusation, he furiously crossed both of his arms and slumped back against his side of the corridor, eyes glaring down the hall at nothing in particular. Honestly, the kid's words had cut straight through the heavy tension and made Sam's heart ache almost as much as his arm did. Ouch. Did Oliver really think that Sam _hated_ him? Sam may have been upset in the past and made things needlessly difficult for everyone, but that was because Sam was struggling with his own role of being a father. Sam wanted to be Jessica's protector, caretaker, doctor, friend; her everything. And Oliver just happened to be the guy who held Jessica's heart just a little bit tighter than Sam did... A few more moments of uncomfortable silence went by before Sam finally cleared his throat.

“Oliver,” he began softly, “I don't hate you.”

The red-haired kid gave a single, humorless laugh and shook his head.

“Sure,” he muttered.

“No. I mean it,” Sam went on, pausing to get his words right as the weight of his own guilt grew heavier, “I... I'm sorry I've acted like an asshole toward you. You never deserved it... I was just selfish. I wanted to keep my daughter's heart all to myself. And seeing her give you so much love made me... well, it made me... a little jealous,” Sam carefully admitted, feeling shameful, “I never hated you, man. I only hated the thought of having to give my daughter to you one day...”

Thankfully, Oliver's head slowly raised and a calmer expression started to creep over his freckled face in the dark. Sam gave him a half smile when their eyes met again.

“I'm actually grateful that you're with Jessica, Oliver. I swear,” Sam nodded, still cradling his own arm, “You're a good kid with a good heart. There's nobody else I would rather see Jessica get married to.”

The mention of marriage created an uncomfortable shift in the air. Oliver let out a breathless chuckle and shook his head again, sliding his knees up to his chest to loosely hug them.

“Oh, you won't have to worry about that. We're not getting married,” the kid denied.

Sam almost felt his own head tilt to the side. Wait. What? Oliver wasn't getting married? What the hell did that mean? After trying – and failing – to gather the answer from Oliver's silence, Sam felt the need to ask the question out loud.

“Um... what?” he gently pressed.

Oliver shrugged against the corridor wall as if he was calm and collected, but his fingers were nervously fidgeting with the tiny rip in the knee of his jeans.

“I'm not going to marry her,” he said, his brown eyes glancing around, “I would never put her through that.”

“Put her through what?” Sam asked, still trying to understand the kid's thought process.

“Through marriage,” Oliver stated, his voice shallow, “The whole 'marriage' thing is just a bad idea. I mean, Jessica and I hardly fight right now, but if we got married, we would be fighting all the time. We would just tear at each others' feelings until we didn't love each other anymore. And I don't want to be that guy, you know? The one who makes his wife feel bad about herself? I don't want to make Jessica feel bad. I never want to stop loving her. So I'm not gonna marry her.”

Oliver turned bashful all of the sudden and hid his face behind his knees. The action made him look like a little kid, and staring at the shy red-head made Sam realize what was happening. It sounded like Oliver hated the idea of marriage because of what happened to his own parents. Sam didn't know the whole story surrounding what happened between Jane and Eddie Thompson, but whatever went down had a lot of affect on their son. Oliver must have seen and heard his parents do and say things that no child should have had to witness. Their divorce was nasty between them, but it was even worse for their child who was caught in the crossfire. Sam had no idea that Oliver's parents' divorce had changed his outlook on the very idea of marriage. It was no wonder why he hadn't proposed to Jessica yet. He didn't ask her to marry him because he thought that marriage turned relationships sour...

Sam glanced down at his swollen left hand, where his own wedding ring was tight around his finger. Growing up with a single father, Sam didn't know much about marriage. Everything he learned about it came from his _own_ marriage with Gabriel. Yes, there were fights – many of which started because Gabe got restless and felt the urge to be a trickster... But there was so much more to marriage than just a few arguments. Love was the foundation of their marriage, but it was also built with compassion, forgiveness, understanding, and the willingness to let someone else be right sometimes. It was a constant give and take. And, in the end, both of them were better for it. Sam knew that he was a better person because of Gabriel's companionship and everything they had been through together. By now, Gabriel was literally the other half of Sam's soul. Marriage defined their relationship in the best possible way... and it could be that way for Jessica and Oliver, too.

After he gathered his thoughts, Sam knew that he needed to share them. The only problem was getting Oliver to listen and take it to heart. Why would the kid want to listen to Sam now, after everything he'd done?

“Hey,” Sam began as peacefully as he could, “Marriage isn't all that bad.”

“Uh-huh,” Oliver muttered, refusing to look at Sam properly, “Tell that to my mom and dad.”

Sam swallowed hard. He knew that was the reason the kid was upset, but hearing it out loud still hurt.

“I can't speak for _your_ parents, but _Jessica's_ parents have been happily married for nearly eighteen years now,” Sam smirked a little, “Gabe and I have been through a lot, but we've made it. You already know that, Oliver. You've been there to see it.”

“Yeah, but you're not...” Oliver trailed off.

When the kid didn't finish his words, Sam felt worried.

“Not what?” he carefully pressed.

Oliver sighed and dropped his knees to sit Indian style on the floor so that he could look at Sam properly.

“You're not like my dad... But _I_ am,” he finally admitted, “Mom always says that I look just like him. I always dress like him, and talk like him... I do love my dad, Sam. But he's not a nice guy. I know that. He's a jerk to everyone, especially girls. And I'm afraid that -” he stopped short to gulp and look down, “that if I marry Jess, I might end up being mean to her. Like he was to my mom.”

Sam couldn't help but feel a strange sense of deja vu. Somehow, he knew exactly how Oliver was feeling. Sam spent most of his life trying not to be like his own father. He thought that going to college and getting away from the hunting life would spare him the grief of turning into John. Luckily, Sam was nothing like his old man. And neither was Ollie.

“Oliver. You are nothing like your father,” Sam boldly encouraged, “I'm not just saying that to be nice, man. You and Eddie might look alike, but the difference between you is night and day. I agree, your dad can be an asshole sometimes, but that doesn't have to be you. _You_ get to decide who you are. It's all in the choices you make. And if you choose to marry Jessica, I guarantee it'll make you realize how much better you are than your dad.”

Sam's words must have come as a comfort to Oliver, because he slowly nodded and smiled the tiniest bit.

“Besides,” Sam sighed, “Jessica has been in love with you since she was three years old. She knows exactly what kind of person you are, and she adores every bit of you. Believe me, my daughter is dying to spend the rest of her life with you, kid.”

A genuine smile lifted Oliver's face as he glanced toward the dark floor.

“The rest of her life? With me?” he muttered bashfully, “I... I never thought about it that way...”

Oliver shared another look with Sam and the two grinned at each other. The one thing that always seemed to divide them was also the one thing that brought them closer together. And that was Jessica... A few howls of agony echoed down the hall, briefly interrupting the guys' conversation. The two of them looked around and burrowed against their respective sides of the corridor, both trying to blend in as seamlessly as possible. They remained as quiet as they could until the anguished sounds stopped.

“Do you think Gabe and Jess heard us praying to them?” Oliver asked in a nervous whisper.

“Don't worry,” Sam assured, gently coddling his broken arm against his chest, “They'll find us.”

No sooner than Sam finished his sentence, a golden light suddenly sprang from around a distant corner and grew brighter as it blazed a trail straight toward them.

* * *

Jessica barged into her uncle Bobby's house and ran back into the study as fast as she could. Her loud and sudden appearance caused every eye in the room to look toward her, even uncle Crowley's from the couch.

“Th – they're gone!” she sputtered, pointing toward the door behind her as she looked to her Papa, “Dad and Ollie! The – there's a trap on the floor but the portal to Hell is broken! And they're gone!”

“What trap?” uncle Dean asked.

“The portal's broke?” Bobby repeated.

“Yes!” Jessie shrieked, “It looks like they tried to summon the warlock or something, but the garage is empty and the portal is broken! Could they be in Hell? How are we going to get to them, Papa?!”

“Oh, shit. Hell? We can't even hear prayers from there,” Papa gasped, turning white as his golden eyes flickered to the demon on the couch, “Uh, Crowley? You got an extra magic door somewhere?”

Crowley wheezed heavily and gripped the couch in pain before shaking his head once.

“N – no. That was the only one,” he groaned.

“And I'm guessing you can't teleport there, either,” Papa continued.

“Oh, in this state of absolute peril? _Of course I bloody can't_ ,” Crowley hissed, though his eyes suddenly lightened and flew toward Jess, “but, Jessica, darling... I believe you might be able to.”

“M – me?” Jess breathed, “How?”

Crowley paused to grimace and hold his stomach before waving her closer. Jessie quickly stepped up to the edge of the couch, where her uncle Crowley reached out to take her hand. Jess immediately noticed how weak and cold his fingers were.

“All you have to do is picture my throne room,” he began, “The castle works as a... teleportation device, of sorts... I believe with your high-powered grace, you may be able to fly there... Just picture it in your mind, love. And let the grace do the rest for you.”

Jessica nodded to confirm the instruction before closing her eyes to concentrate. She had only been inside Crowley's throne room one time. But it was such a distinctly unique place that she had no trouble remembering large portions of it. The throne itself was what she remembered the most, along with all the onyx display cases. Once she had a good vision of it in her mind, Jessica allowed her grace to work; feeling the outline of her wings spread a little to prepare for flight. It was no different than flying around on earth.

But when Jess opened her eyes again, she was facing her uncle's dark, empty throne room.

Everything was still, silent, and dark as night. The candelabras in the corners weren't even lit. Jessica held up her own hand and allowed her golden grace to shine and light up the room enough to see where she was going. She had hoped that her dad and boyfriend would be there, but they weren't.

“Ollie?” she called out, “Dad?”

When she didn't receive a response, Jessica carefully ventured further through the room. It was strange to see a place like this so vacant. She was expecting to at least see a few demons or hell hounds, but there was no one. Where had everyone gone? Were they out trying to find Crowley, their king? Or were they busy torturing souls?

Jessica was so spooked by her surroundings that she didn't even call for her dad or Ollie again. She just walked around Crowley's black castle-like home as quickly as she could, lifting her grace-lit arm high in the air to search for them. The many corridors made her feel like she was trapped in a maze. For a while her own fast footsteps and heavy breathing were the only sounds around her. Jessica was beginning to lose hope that her boys were even there at all – until she spotted a pair of legs down the hall in the distance.

On instinct, Jessica practically ran down the corridor. As she sprinted, the light from her hand illuminated the space to reveal two of her favorite faces in the whole world.

“ _Dad! Ollie!_ ” she gasped.

“See?” Dad muttered toward Oliver, “Told ya.”

Jessica was so happy to see them that she didn't even stop to comprehend what her dad was saying to her boyfriend. She just knelt down in the floor to wrap Oliver into a hug first.

“Oh my God!” she breathed, squeezing Ollie so tight that she could practically hear his heartbeat, “I was so worried! Wh – what happened?!”

Ollie glanced down in defeat as he opened his mouth.

“I... I screwed up,” he admitted, “I tried to summon the warlock and he threw us in Hell...”

“Actually, it's _my_ fault we're here.”

Jessica and Oliver both looked across the hall to her Dad, who was nodding with shame.

“I interrupted Oliver when he was saying the ritual, so it's pretty much on me,” he explained, suddenly biting down a groan as he held his arm, “and my arm was broken in the process.”

Jessica gasped and instantly crawled over to give her dad's arm a healing touch. With a tiny bit of her grace, she was able to mend his broken bones and relieve his pain. He flexed his arm afterward and gave Jess a smile.

“Thanks, baby-rabbit,” he nodded, “How did you get here?”

“I flew,” she admitted climbing back to her feet and holding out her hands, “Here, hold on to me. I think I can take us back.”

Obviously not wanting to be there any longer than she did, Dad and Ollie both jumped up to hold Jess's hands. Once she had a hold of her father and boyfriend, Jessica closed her eyes and pictured Bobby's kitchen again. In the same way she had teleported to Hell, Jessica flew herself back out; appearing back on Earth within seconds. Admittedly, the flight between realms did take some of her energy away. And when they reappeared back home, Jessica instantly slumped against Oliver's tall form. He, of course, wrapped his arms around her to keep her on her feet, but looked down at her with concern.

“Jessie, are you okay?” he asked.

Looking up at Oliver's cocoa eyes – and knowing that he was completely okay – nearly overwhelmed her. Jessica bit her bottom lip and nodded before fully embracing her boyfriend with a tender hug. Ugh, she didn't know what she would do if anything ever happened to her Ollie-pop...

“D – don't ever leave me again,” she whispered in a cracking voice.

Oliver's arms tightened around her back.

“I won't,” he replied, “I promise.”

While the two of them lost each other in their meaningful hug, Jessica could hear Papa rushing in to meet Dad.

“Moose! What happened?! Are you okay?!” Papa gasped, pulling on Dad's sleeve, “Where did you go?! Did you get hurt?! Take your clothes off, lemme check you for injuries.”

“Gabriel, I'm fine,” Dad promised, wrangling his arm back, “What happened here? Did the warlock come in?”

“Warlock?” uncle Dean said, “No, we haven't seen the warlock. We thought you guys botched the ritual or something. Was he not in Hell with you?”

“No,” Dad answered, “He was out in the garage when we last saw him. Oliver and I thought -”

“P – Pop?”

Everyone in the room turned to look toward Jude near the desk, who had just interrupted Jess's Dad with a weak and worried tone. Jude was looking toward uncle Cas, but his face was eerily pale. His fingers were nervously fidgeting and it seemed like he was almost on the verge of tears. Cas immediately raised up from Dean's side to look at Jude properly.

“What is it, son?” Cas asked.

Jude bashfully looked around at all the people in the room, lingering on Crowley and Bobby before looking back to his Papa.

“I can't find Clarence,” Jude squeaked.

 

**Notes for the Chapter:**

> Eek! Sorry for the cliffhanger, everyone. I just couldn't help but elude to next week's chapter a bit. ;D I think it's safe to say that Sam and Oliver might finally be on the same page. That open and honest conversation they had in this chapter has been due for a long time coming, and I thought that there was no better place for them to have it than in Crowley's kingdom. XD I figured that Oliver's experience with his parent's divorce would affect his decision to propose to Jess, which is why he hasn't popped the question yet. But after his talk with Sam in this chapter, I think his outlook may be changing soon. ;) I hope you all enjoyed this emotional roller coaster! :D And I hope you had a great Halloween this year. Thank you so much for reading and commenting! The next chapter – which will star Clarence and Jude – will be out soon! :)


	9. Chapter 9

**Notes for the Chapter:**

> This chapter gets pretty heavy, folks. Brace for some feels!

From the time he was little and all the way through his shitty teenage years, Clarence rarely ever thought about having a father. He had so many moms around – all seven witches that took him in, plus the real one he was searching for – that he didn't care about having a dad. It never really occurred to him that there might be some man out there that looked and sounded like him. And once Crowley confirmed his father's death all those years ago, Clare had a defined answer. The guy was dead. Good. That meant the 'family drama' was over before it had a chance to begin. Clare never wanted to meet the guy anyway… or so he thought.

After actually seeing his father in person and getting to talk to him, Clarence felt disturbingly confused. The rapist, demon killer – the man responsible for messing up Meg and Clare's entire lives – admitted that he actually _wanted_ to be Clare's father. He was the reason Clarence was alive; not just because he knocked up his mother by accident, but because he let them both live out of love. _Love_. God, that was such a strange thing to hear a raping murderer talk about. But he sounded so genuine when he spoke, like he actually wanted to know about Clare's whole life...

But now, as he crouched on the floor near the dying king of Hell, Clarence had just received news that stirred his own suspicion and confusion even more. Jude and Jess's dads had returned from their meeting with Death to tell everyone that the warlock lied. Clarence's father had lied. The curse _did_ belong to him, and Death had no reason to cover for him. Once Castiel said it out loud, Clarence could feel every eye in the room glance toward him. Of course, they were all worried and concerned that he would be upset about hearing that his father was a liar – but Clare kind of saw it coming. Of course the asshole was a liar. Every other man from Clare's past was a liar. What made this shit-heap different from the others?

Still, the longer Clarence sat there and thought about it, the more he could feel his own heart hammering in his chest. Clare could deal with his father being an asshole. If the guy was just a raping, murdering, lying sack of shit, Clarence could handle that. In fact, it would have made things so much easier, because then Clarence could unabashedly hate him... But that conversation they had – the one where Caldwell told his story, explained that he actually cared very deeply for Clarence, and that he was sorry for everything that had happened to him – made it _so much harder_ to hate him completely. There were so few people in the world that actually gave a damn whether Clare was alive or not. How the hell was he supposed to ignore one more? Especially when that person was his own father; someone who could give him insight into his real family's heritage, and maybe even give him a clearer picture of who he was?

“Jude.”

Jessica's high voice pulled Clarence out of his deep thoughts. He looked over to see Jess handing Jude the bowl of healing mixture and gauze she had been using.

“I'm going to go find Dad and Ollie. I'll be back as soon as possible,” she explained.

Watching Jessica get up and walk out of the study made Clarence want to do the same thing. He wanted to get up and move around; get the blood flowing to his brain better so that he could think more clearly. The demon took a short breath and shifted around on the floor, reaching out to clutch Jude's arm as he rocked himself to stand.

“I'm gonna take a walk too,” he mentioned to his angel in a whisper.

Of course, as soon as Clare stood up, Jude copied him. The guy seemed determined to follow Clarence wherever he went, like he was waiting for him to talk about everything that was happening.

“Um, okay,” Jude breathed lightheartedly, “Where do you want to -?”

“Jay,” Clare interrupted with a sigh.

The demon turned around to face his fiance, whose beautiful blue eyes were filled with concern. It was so painfully clear that Jude wanted to take Clare's pain away. But Clare knew he couldn't. Not this time.

“I'll be alright,” Clare promised, reaching up to briefly caress Jude's soft cheek, “Just... gimme some time, okay?”

Jude eventually nodded, but the shimmer of concern in his eyes faded to disappointment. Clare absolutely hated upsetting Jude, but he didn't want to lie to him either. Clare just needed a minute to himself and he hoped that Jude would understand. Luckily, the blue-eyed angel stayed in the study when Clare started to walk away. He wasn't heading in any particular direction. He just needed to be alone long enough to figure out how he was feeling.

Clare's wandering feet led him all the way through the house to his own bedroom, where everything was placed just the way he left it. Full-sized bed perfectly made, dresser drawers neatly closed, boots and shoes lined against the wall near the door, guitar on the stand near the bed, shelf of potions and ingredients untouched, lamp in the corner lit, snapshots of him, Jude, Jessica, and Oliver peppered on the mirror... Clarence's room was clean, quiet, and inviting, just the way he liked it.

The demon sighed as he closed the door behind him and walked over to the end of his own bed. As he lowered himself to sit, however, Clare was overcome with a strange sense of despair. This bed wasn't really his, was it? This house and all the people in it; they weren't really his family. Not by blood. No, his real family consisted of vengeful, cold-hearted liars, cheaters, drug addicts, and God only knew what else. Clarence could make-believe all he wanted to that he was part of the Singer, Winchester family, but in truth, he was bound to the sadistic likes of his real mother and father by blood... The door suddenly opened across the room and he exhaled a sigh. He knew it wouldn't be long before Jude came looking for him.

“Jude,” Clare grumbled, pulling himself up from the bed to look to the door, “I told you I just need -”

Clarence's voice faded out as soon as he registered the face he was looking at. It wasn't the perfect, blue-eyed, freckled face of his fiance – but the scarred, aged, untrustworthy features of the warlock he had spoken to hours before. Clare could almost feel the blood draining from his own cheeks as he watched the warlock enter his room and shut the door behind him. Holy shit. The guy was alive. And he was standing inside Bobby's house. _The same house Crowley was dying in_! What the hell was he doing here?!

For a second, the pair of men just stared at each other; Clarence with shock and Caldwell with the most innocent look ever. Clare felt the urge to call for someone – preferably Jude – but he couldn't find his voice. The moment he opened his mouth, Caldwell cut him off anyway.

“I know,” the warlock spoke calmly, raising his hands in surrender, “I've invited myself into your room without asking for permission. Forgive me. I only wanted to see you again. And perhaps talk, if you're willing... Son...”

Clarence gulped hard, feeling his own Adam's apple 'thunk' in his throat. The warlock seemed genuinely interested in speaking to Clarence – but why? Why would he want to talk to Clare? To get information from him? Create some evil master plan? … or was it really just to talk, like a parent who wanted to learn about their long-lost child? Looking at the warlock's face – masculine features that undeniably resembled his own reflection – almost made Clare forget about the big picture. He almost forgot about all the trouble happening in the study. But glancing toward his jacket hanging on the back of the door, the black one that Crowley bought him, made him remember.

“You lied,” Clare immediately pointed out, finally regaining his voice to accuse the man in the room with him, “That's not Death's curse. It's yours.”

Caldwell took a deep breath and looked away but slowly nodded.

“Yes. I'm afraid that's true,” he admitted, “I did lie... but only to fool those hunters. I've dealt with their kind before. I know how to keep them running in circles -”

“Break it,” Clare demanded, thinking of Crowley suffering in the study.

Again, Caldwell paused to take a breath. He seemed exasperated by Clare's repeated defense of the king of Hell.

“Clarence, my boy, it's not that simple. Curses are complicated matters -”

“No, they're not,” Clarence instantly corrected, “Every curse, every hex, every spell has a counter. I know magic.”

“Indeed, you do,” Caldwell smiled, casually shuffling over to gaze fondly at the shelf of potions and ingredients nearby, “Hemlock, Lady's Mantel, Sage, Betony... These are advanced materials. You're quite the brewer, aren't you?”

Clare didn't answer. He only stared at the man apprehensively, still too angry – and confused – to properly respond. Since Clare never spoke, Caldwell stepped toward the guitar on the stand, pointing at it with a warm smile.

“And you play the _guitar_ ,” he hummed, wearing the face of a truly proud parent, “Beautiful instrument. Poetic. Almost makes your fingers dance with the music as you play... I understand that feeling. I play the piano, you know. Perhaps a love of music is a trait that we share.”

Clarence clenched his jaws as tightly as he could. He felt a very strong urge to ask the man – his father – about his musical experience; about where he learned the piano, what he liked to play, his favorite song... but Clare made himself hold it back. ' _He's a monster, remember?_ ' The voice in his head reminded bluntly, ' _He's not your friend. He's a murderer._ '

“Why are you here?” Clarence asked.

He figured that was a reasonable thing to ask the warlock. After all, the house they were standing in was full of people who wanted to kill him. Why would he risk coming here? Surely it wasn't just to talk to Clarence about music, was it? Surprisingly, when Caldwell turned around face to Clare, he was still wearing a pleasant smile.

“I came to see you, Clarence,” he spoke sincerely, “and offer you a gift.”

Everything in Clare's mind was telling him not to trust this man. Clare's entire body was demanding that he announce the warlock's presence in the house and let the Winchesters deal with him... but his heart – the weak, needy organ beating in his chest that always ached to know a real parent – was actually kind of excited. Caldwell had a present? For him? What was it? Against his better judgment, Clarence heaved a sigh. The defeated sound and inadvertent surrender seemed to make Caldwell very happy. His smile brightened and he tilted his head.

“It isn't here, though. I'd like to take you to it,” he explained, his smile dimming at the sight of Clare's immediate hesitation, “Though, if you don't want to go anywhere alone with me, I'll understand. I know I'm a stranger to you, and that you have no reason to trust me... but I feel like you would really benefit from this trip. I'll leave the choice with you, son. I won't force you.”

Clare could feel his lungs working hard inside his own tight chest. Shit. Why did the warlock have to do that? Why did he have to make himself sound so sincere? How could he make a gift sound so damn enticing? As he took a moment to glance around his room, Clare realized that he really wanted to go. He wanted to see what kind of 'gift' his real father had in mind. For all he knew, it could have been a trip to Disney World or some shit; a happy, fun place where they could really bond like father and son. Of course it was dangerous to trust the guy – but Clarence knew he had a fail-safe. There was always one thing he could do if he ever found himself in danger. All Clare had to do was pray Jude's name, and Superman would come swooping in to save him. If needed. With his fiance just a prayer away, Clarence saw no problem in going with the warlock.

“... Fine,” Clare reluctantly allowed, “But you bring me back here afterward, okay?”

“Yes, of course,” Caldwell nodded, bubbly with delight as he reached into his pocket, “I'll make it quick, son. You don't have to worry. I promise.”

Clarence watched closely as the warlock withdrew his hand and tossed some powder to the floor. It created a thick smoke that instantly swirled around the two men in the room. Clarence covered his mouth and coughed, afraid of inhaling the dark cloud in case it was poisoned or something. But the smoke soon cleared – and Clare's bedroom was gone.

Once he was able to see through the dissipating haze, Clarence could see a line of houses on a darkened street. The sounds of a city were humming nearby – familiar noises of distant cars, sirens, and subways that Clarence recognized from his childhood. Only, he didn't know the neighborhood he was standing in now. It almost looked abandoned. Even the streetlights had been knocked out. It was dark and sobering here, apart from a few dimly lit windows in the houses. Clare sort of recognized those, too. With the graffiti-scribbled siding, broken windows, tall grass, and faint smell of weed, Clare assumed that these were crack houses; abandoned places where people congregated to get high and sleep. Why did the warlock bring him here? Instead of asking the question out loud, Clarence only looked to the man next to him and shrugged his shoulders in confusion. Caldwell gave a firm nod of understanding before reaching over to carefully curl his arm around Clare's shoulders and pull him forward.

“This is an outlying suburb of New York City,” the warlock explained, gently leading Clarence toward the front door of the house in front of them, “Clarence, when I asked you to tell me about your life, you mentioned all of the... painful horrors you went through. And I have to tell you, it broke my heart. Knowing that you, my innocent child, had to endure senseless abandonment and rejection, well... It forever changed me. My heart now belongs to you, too.”

Clarence wasn't sure how to feel. Hearing Caldwell say those things was nice, but what did any of it have to do with this crack house? Clare braced himself as the warlock opened the front door and gently pulled him inside. The house wreaked of urine, rotten food, and general nastiness of unclean people – something else that Clare became accustomed to in his youth. There were a few sleeping people that he and Caldwell had to step over in the dark, but no one moved. They were all too high to even notice them as they walked by to get to the stairs.

“You said that you lived on the streets,” the warlock continued, his voice filled with pain and slight anger, “No home or family... Having to do extremely risky things to stay alive... That chills me to my very core. If I had the power to turn back time, I would have rescued you, son. I would have saved you the terrible fate of living through all of that... But while it's not in my power to change the past, I can offer you something else.”

By now, they had reached the top of the stairs and turned down the hall, where they stopped by a certain door. It was closed, but the outline of it was lit; as if there was a lantern or candles burning inside. Caldwell paused to gently hold Clare's shoulders so that he could look down into his eyes in the dark.

“Tell me, Clarence,” he said quietly, “When you finally found your mother, and she told you that she cut you out of her womb and tossed you over a bridge, how did you feel?”

Clarence gulped hard again. He didn't see why any of this mattered. What did his past have to do with this crack house? Why were they there, talking about this stuff? Though he was confused as hell, Clare decided to answer the question.

“Angry,” Clare breathed, remembering how badly it hurt, “Rejected... Unwanted... Pissed as hell...”

“Yes,” Caldwell nodded, “and _why_ did you feel that way?”

“B – because she said she didn't want me,” Clare recalled, feeling a lump trying to form in his throat, “She kept calling me 'it'. I... I was just the thing she never asked for...” he breathed, feeling tears trying to rise in his eyes, “Sh – she didn't even name me... I got my name from a note she wrote to someone else. How messed up is that?... God, she wouldn't even _look_ at me...”

Caldwell nodded and patted Clare's shoulder, comforting him with a soft gesture.

“Hold on to that feeling, Clarence,” he instructed, carefully letting go to slowly reach behind him, “It will help you get through this rehabilitation.”

Clare narrowed his eyes. Rehabilitation? What the hell was he talking about? Before Clare could ask, Caldwell opened the door behind him and moved to the side, allowing the dim light inside to catch Clare's eye. It was coming from a small group of candles that were on the floor, near a dirty old mattress. And though the light was barely able to illuminate anything, it did help Clarence see the person laying on the mattress... It was her. Meg. The same woman they were talking about. Clarence's mother. She was laying unconscious on the mattress with several empty syringes tossed near her limp, track-marked arm.

Agonizing discomfort and dread flew through Clarence instantly. Holy shit, it was really her. Clare had only seen Meg one time, but it was more than enough to burn her face into his memory. The demon only blinked down at the unconscious, boney, barely alive woman on the mattress, wondering what the hell he was doing here. He shifted his pained gaze to Caldwell for the answer.

“After that angel killed me and Death revived me, I immediately went searching for her,” the warlock explained, voice low, “so that you could enact your justice.”

“J – Justice?” Clare repeated, his voice so faint that even he could barely hear it.

“You said it yourself, son. She cut you out and tossed you aside,” Caldwell reminded, pointing to the frail person in the room, “That woman there inflicted endless suffering upon you. If it wasn't for her selfish apathy toward you, you would have had a mother. A home. A good life. Instead, you were lost to the streets, left alone to wander aimlessly through a terrible life.”

Clare opened his mouth, but he couldn't deny what the guy was saying. Caldwell was right. Meg really did shove him into a shitty life by doing what she did...

“Think of all those things you went through,” Caldwell encouraged, his voice still low but full of passion, “Remember the losses you've had. Those witches you mentioned? They are gone. That mother you went searching for? She didn't want you. She would rather you struggle to find food, shelter, and affection than to simply be there to care for you. So many things you didn't get to experience. So much love you never received -”

“ _Why_ ,” Clare hissed, feeling a hot tear race down his own cheek as he glared at the warlock, “ _Why are you saying this shit?!_ ”

Caldwell stood proudly and brought his hand forward. There was a long, black blade in his hand, one that he offered to Clarence.

“So that you can taste the pure, all-encompassing relief of vengeance for yourself,” the warlock spoke boldly.

Clare's mouth remained wide open, this time in surprise and horror. Damn. Did Caldwell actually want Clarence to _kill_ Meg? Is that what this 'rehabilitation' was? Did he think that killing her would bring Clarence peace or something?! No! It wouldn't bring him peace! Only more guilt; guilt he didn't need! The demon immediately pushed the warlock's hand away and shook his head.

“N – no,” he denied, though there were tears falling down his cheeks, “Screw that.”

“Vengeance is what you need Clarence,” Caldwell quickly continued, still trying to force the blade into Clare's hand, “Take it from me. Once you've plunged a blade into the person responsible for everything that has gone wrong in your life, you can begin to heal. Just as I did.”

“No,” Clare said again, hearing that his own voice was getting higher with anxiousness, “I can't -”

“You can,” the warlock insisted, turning to point at Meg again, “Look at her. She is barely alive anyway. You would not only be ending your own pain, but hers as well.”

“ _No_ ,” Clarence barked loudly, “I'm not going to hurt her.”

“Even after everything she's done to you?” Caldwell pressed, “Even after all the pain she's caused? Come now, son. You _know_ that ending her life is the right thing to do!”

“It's not the right thing!” Clare argued, “God, I can't believe I let you bring me here. Take me home. Now.”

“Clarence, heed my words,” Caldwell pleaded sternly, “You will never fully heal – you will never be whole – unless you remove the poison of this woman's life. Here,” he held out the blade again, “Take this and kill her. End the pain. Here and now.”

Clarence was barely aware of his own panting as he stood there and gazed between the black blade in the warlock's hand and the unconscious demon on the mattress. The only thing he could think about was how crazy the warlock bastard sounded. Murdering someone wasn't a way to heal! Clarence could never live with himself if he knew he had been responsible for his own mother's murder, no matter how shitty of a parent she was! There was no way Clarence could even bring himself to hurt her, let alone kill her – because he had been in the exact same spot she was in now. Clare knew exactly what it was like to get as high as possible and try to sleep life away. He had been an addict, too. Clare and his mother were more alike than he thought...

Strangely, just as the thought crossed his mind, Clare noticed that Meg's weary eyes were blinking slowly.

Panic flooded Clare's body like a broken dam. Oh, shit. She was _awake_. Meg could hear everything that they were saying! Clare didn't want to be here! He didn't want to be in the same room as his birth parents anymore! He just wanted to go _home_! Still, the warlock tried to force the weapon onto Clarence.

“The quicker you do this, son, the faster the healing can begin,” Caldwell breathed.

“For the last damn time! _I said no_!” Clarence nearly screamed, “I'm not doing it! I'd never hurt her! And screw you for even bringing me here!” the demon quickly turned to close his eyes shut tightly, giving himself some privacy as he began to pray, “J – Jude, please come and get me. I don't want to be here anymore -”

“ _No_ ,” the warlock gasped, taking Clare's shoulder and spinning him around, “You cannot let those angels interfere! They are not like us, son! They won't -”

A sudden, blinding flash of light burst into the room and Clarence immediately buried his face into the crook of his own arm. The warlock's sentence was cut off – because he was tossed through the room. Clare heard his body hit the far wall with a thud. The bright light dimmed and Clarence felt a soft pair of hands on his arms.

“Clare?” Jude's beautiful, timid voice asked, “Are you okay?”

Clarence was so overwhelmed by the sound of Jude's voice and the sight of his handsome, familiar face that he almost burst into tears again. Jude had flown to his side and blasted Caldwell across the room, even though he hated flying and fighting more than anything. The demon nodded to answer the angel's question, but before he could speak, he noticed a figure running toward them. Caldwell had gotten up and was now running toward Jude – with the blade raised over his head.

Clare barely pushed Jude out of the way in time for the warlock to come barreling at them. He ended up running between them and ending up on the other side of the room, near the window. Seeing the warlock charge toward them with a weapon must have pissed Jude off, because the angel's blue eyes and clenched fists suddenly electrified with grace and he turned to expel a huge ball of light toward Caldwell. The warlock turned just in time to be engulfed by the light, which swiftly tossed him through the glass behind him.

After Caldwell broke through the window and disappeared, a painful scream echoed from outside. Clare instantly raced over to steal a peek out of the window pane, wanting to see what had happened. Caldwell was unmoving, laying flat on the grass below... with his own blade sticking out from his back. Clarence gasped and covered his mouth, shutting his eyes and turning away from the window in horror. Shit. The warlock had fallen on his own blade. Oh, God. Did that mean he was dead? Would Death bring him back again? He had to, right? Before Clare could get too upset, Jude took his hand.

“He's gone,” the angel muttered, “It's okay, Clare. He's not there anymore. You're safe.”

The demon forced his eyes open and searched Jude's beautiful face, seeing worry and consolation in his eyes, before turning around to look out the window again for himself. Jude was right. Caldwell's entire body had disappeared, just like when Castiel killed him at the bunker...

A quiet creak on the floor boards caught Jude and Clare's attention. They both turned to see that Meg, the demon who was completely unconscious just moments before, was now sitting up on the mattress. She was heavily medicated, barely keeping her head up and blood-shot eyes open, but she was slowly blinking at the two men in the room with her. Seeing the woman's hollow face again – along with remembering the last time he had seen her in person, and all those horrible things she said – made Clarence nearly bite his own bottom lip off to keep the tears inside. He instantly threw himself at Jude, twisting both arms around the angel.

“Take me home,” Clare begged, holding onto Jude for dear life, “P – please, Jay, _take me home_.”

Without another word, Jude's arms came up to circle Clare's back and he could feel the chill and stench of the crack house morphing back into the warmth and woodsy-smell of Bobby's. He didn't open his eyes, though. He didn't want to look up, afraid that he might see his doped-up mother staring back at him. Clare only locked his arms around Jude and refused to let go.

“C – Clare?” Bobby's worried voice was close by, “Oh, thank God, you found him!”

“Where was he, son? Is he alright?” Castiel's voice was just as concerned.

“The warlock took him. But he's alright, now,” Jude assured, as he began walking Clarence away from the voices, “He... He's been through a lot. I think we should give him a few minutes to calm down.”

Wow. Jude knew Clare so damn well. The kid understood that Clare didn't want to be interrogated by their family. But Clare didn't want to be _completely_ alone. Not immediately, anyway. Clare opened his eyes long enough to see that they were heading toward his bedroom and he tightened his arms around Jude.

“Stay with me, Jay,” he asked breathlessly.

Jude opened the door and led the way inside, where he closed the door again behind them and continued to rub his hands up and down Clare's shivering back.

“Of course I'll stay with you,” Jude whispered, “I'm your future husband, after all.”

The mention of their private nickname for each other was probably meant to be playful and uplifting. But this time, it chilled Clare to the bone. Poor Jude. The kid was headed toward a dark future.

Because he was going to have to marry Clarence some day...

* * *

Jude wasn't sure how long he and Clarence sat silently in Clare's bedroom, without speaking or letting go of each other, before someone came to the door. The angel assured his demonic fiance that he was only going to tell their family that everything was okay before stepping over to peek his head outside. Dad, Papa, and uncle Bobby were all standing in the hallway, wanting to know exactly what happened. And although Jude wasn't entirely sure why the warlock and taken Clarence to that place – to the old house where Clare's real mom was – he did know a few things for certain. He told them everything that happened when he rescued Clare.

Jude relayed as much information as he could to his parents and uncle, who, in turn, told him that they were about to set their plan to kill Death in motion. Dad said they had brain stormed and came up with an idea, but it was going to be tricky to pull off. But Papa requested that Jude stay with Clarence and keep him safe, just in case the warlock came back, and Jude was determined to do the job well. He wasn't going to leave Clare's side until that warlock was dead, once and for all.

After their parents left the door, Jude immediately returned to Clare's bed to be with him. He was clearly shaken up; eyes wide and vacant, as if he was lost in thought. To comfort his distraught fiance, Jude gave the edge of his mouth a kiss and pulled him to lay down on the bed. Though Jude was very curious about what happened between Clare and his real parents before he showed up, he knew that Clare didn't want to talk about it right now. And Jude didn't want to push him into it, either. The angel simply cuddled the demon on the comfy bed, holding him close and tenderly as they listened to the distant chatter of their family down the hall.

The two of them laid that way for hours; chest to chest, fingers tangled, faces nuzzled against each others' shoulders. The mixture of silence, warmth, and the sound of Clare's steady breath was so comforting to Jude that he eventually drifted to sleep. It was only a cat nap. Jude was only out for maybe half an hour at the most. But when he eventually opened his eyes again, the angel realized that his fiance was no longer in the bed with him.

Jude instantly raised his head and reached out to feel the spot Clare had been laying in, noticing that the bed was still a little warm. That meant that Clare had only just left, but where did he go? To the bathroom or something? He wasn't taken by the warlock again, was he?

“Clare?” Jude called into the empty bedroom.

Of course, no reply came. But when Jude turned back to look at his hand on Clare's bed, an entirely different matter caught his attention. The angel nearly gasped and raised his left hand to spread all five of his naked fingers. His ring! His engagement ring! _It was gone_! Panic burst through Jude's whole body as he instantly scrambled to stand up from the bed and pat around his pockets and the black comforter in front of him. Oh God, where did it go?! Jude must have lost it when he was rolling around in his sleep or something! Oh, no, what was Clare going to think?!

Jude almost turned Clare's entire bedroom upside down looking for the shiny ring – pulling out drawers, tossing stray clothes around, digging through every last crease of bed sheets – but he couldn't find it. An absolute storm of anxiety swirled in his chest as he eventually backed up against the door and looked around with tears in his eyes. No, no, no, Jude couldn't lose that ring! Clare had gotten down on one knee and gave it to him!

Though he was tempted to panic, Jude forced himself to remain calm. Finding the ring was important, but finding Clarence first was even more important. After taking a few bracing breaths, Jude exited his fiance's bedroom and searched the hall in a hurry.

“Clare?” he called again, his voice higher and more frightened than before, “Clarence?”

A figure stepped out from the end of the hall and Jude gasped. From the tall, feminine silhouette alone, Jude could tell that it was his cousin. Jessie stepped down the hall to meet him with a calm expression.

“He's sitting outside on the back porch,” she informed quietly.

Jude nodded and silently thanked his cousin with a brief smile of relief before turning to venture toward the back door. While he was happy that Clare was still home and safe, Jude also felt terrible. Ugh, how was he going to break the news to Clare that he had lost his engagement ring? Though he was tempted to cry, Jude held himself together long enough to open the back door and look outside.

Jessie was right. Clare was perched on the highest step of the porch. His back was to the door and he was staring out into Bobby's salvage yard, where the darkness of nighttime was fading to soft purple. It was nearly morning, now. Dew had already set on the grass beyond the porch. Jude gulped as he brought his eyes to the back of Clare's blonde head. He couldn't keep this ring thing a secret. He had to tell Clare as soon as possible.

“Clare,” Jude called.

Clarence didn't move. He only sat there and stared out at the junkyard. Jude hung his head and shuffled a little closer.

“I – I can't find my ring,” the angel squeaked, “It must have slipped off when I was asleep or -”

His voice trailed off when he watched Clare's hand raise up. Jude's silver, diamond filled ring was slung loosely around Clare's index finger. Jude's mouth fell open. Clare took Jude's ring? But why? Why was he playing with it? Clare's head lowered and shook back and forth a few times.

“I shouldn't have given you this,” his low voice replied.

Clarence might as well have stabbed Jude in the heart with that sentence. The angel swayed around a little, clutching his own chest as if he had been physically injured. How could Clarence say that? Why would he hurt Jude like that?

“Wh – what?” the angel breathed in pain.

Clare brought his hand back down to look at the ring they were talking about. Jude carefully shuffled closer to the demon, wanting to see his expression. In order to do so, Jude had to step down a few of the porch steps. Clare's face was blank. He was turning the ring over and over between his fingers, but he wasn't looking at it. His eyes were unfocused, cast aimlessly toward the broken cars in the distance.

“I was selfish,” Clare explained, “I wanted to have you forever... I didn't realize that it meant you would have to take me forever, too.”

Jude swallowed again and blinked at his fiance in confusion, feeling a tiny tear slip down his own cheek.

“Yeah. That's what I want,” he nodded, “That's what that ring means. That's why I said yes. So give it _back_.”

Jude quickly reached over and yanked the small band away from Clare. The demon didn't even put up a fight. He let Jude take it without even looking at him. Once the beautiful ring was safely back in Jude's possession, the angel immediately slipped it back on his finger where it belonged. It twinkled a little in the soft purple light of dawn, reminding Jude of the first time he saw it back in the bunker. Clare was so happy when he first gave the ring to Jude. Why would he want to take it away now? Jude lowered his hand to look at the demon, who was now staring sadly at the glistening, dew-covered ground.

“I figured it out,” he muttered, “I know why I don't like being a top.”

Jude didn't say anything. He waited for Clare to continue.

“It's because I promised myself I would never be that guy,” he explained, almost glaring at the ground, “Every man that ever touched me had to be the top. They wanted the dominance. The control. They just wanted me to lay there and take it. Assholes, all of them. Pedophiles that needed me to be weak so that they could feel like men... and what they did to me, I swore I would never do to someone else. I would never make anyone feel weak just so that I could have some pleasure -”

“Clare,” Jude softly interrupted, kneeling down in front of Clare on a lower step so that their faces would be even, “You didn't do that to me. You never made me feel weak. I wanted to make love to you that way because I wanted to experience it for myself. You're not like those men -”

“Yes, I am,” Clare blurted, scowling harder at the ground, “I'm destined to be just like them. Because _my father_ is one of them.”

The demon paused to finally look up at Jude. The moment their eyes met, Jude could see the eroding, destructive pain oozing from this fiance. Hatred and anger were eating him alive from the inside out, but when he looked at Jude, sorrow and guilt immediately surfaced.

“Jude, you are so blessed. You have the best parents in the world,” Clare said with a shaky voice, “Dean and Castiel are amazing people, and you are just like them. God, you are the definition of what it means to be a good man... so you can't be with me. Because I've only got two paths. I'm either going to be a strung out, barely alive drug addict, or a demon-killing rapist bent on revenge.”

“No, you're not,” Jude denied, shaking his head, “Clarence, you are not going to turn out like either of your parents.”

“I already have, haven't I?” Clare hissed, though he looked on the edge of breaking down in tears, “The only reason I'm still alive is because you saved me from myself. Addiction was going to take me out of here, until you stepped in. So now, I'm left with my father's sadistic legacy. It's starting all over again... I – I'm trapped in a circle, Jude. I'm stuck in a replaying loop of shit. _This circle never ends_. The rest of my meaningless life is already planned out. But I will never, _ever_ let you get trapped inside this circle with me. You can't marry me. It's bad. It's so _bad_ -”

When Clare's voice began to crack, Jude lunged forward to wrap him into a hug. The angel crushed the demon tight against his own chest, cradling the back of his blonde head and clutching the back of his jacket. Despite Clare's heartbreaking speech about needing to be away from Jude, he still hugged him back with all his might; like a scared child holding a teddy bear. Jude's heart throbbed in pain. He _hated_ hearing Clarence say all of these things. The worst part was that none of it was true! Clarence wasn't trapped in a circle. He was free to be whoever he wanted to be! Jude pulled back just enough to take Clare's tear-stained face in his hands.

“Clare, listen. Life, time, history, none of it is a circle. It – it's more like a tree,” Jude tried to explain, “You are given choices, just like different branches, and its the paths you choose that define who you are. No one else decides it for you. Not your parents, not the men who've mistreated you, not even _me_. Clare, this is _your_ life. And you get to choose how it will play out.”

Jude words must have hit home, because a glimmer of hope flashed in Clare's moist green eyes. Jude smiled at his fiance in the faint glow of dawn, wiping away some tears from his cheeks.

“I just want to be there to share it with you,” he admitted, glancing between Clare's wide eyes and trembling lips, “I love you more than anyone. Don't listen to those mean voices in your head, Clare. Don't let them tell you that you're not important, because you are. You're my best friend. My future husband. My whole universe, remember?”

A smile finally spread on Clare's mouth when he heard some of his own words being repeated to him. The remembrance of Clare's proposal and all those sweet things he said were playing in Jude's mind as he finally leaned forward to bring his mouth to Clare's. This kiss was serious, but full of passion. Jude parted his lips long enough to taste Clare's mouth, restoring the familiar taste of young love between them. Clare's hands raised to cup Jude's face on both sides, gently holding him still as they kissed. When their mouths parted, Clare rested their foreheads together so that they could share the same breath as dawn's purple glow faded into pinkish-yellow around them.

“God, I love you, Jude,” Clare breathed.

Jude smiled and blissfully blinked his eyes. He would never get tired of hearing Clare say that...

“I love you too,” he replied, raising a playful eyebrow, “but if you try to take this ring away from me again, I'll have to spank you.”

The subtle joke made Clarence laugh for the first time in a long time, and the sound delighted Jude's entire soul.

“You won't have to worry about that, Jaybird,” the demon sighed peacefully, “That ring never has to come off your finger again.”

 

**Notes for the Chapter:**

> Hey you guys, I'm so sorry for all those feels in this chapter. :( But at least the title of the story makes sense now, right? ;D I know some of you are probably wondering why Caldwell would encourage Clare to kill Meg when he was supposed to be in love with her. It's probably not a spoiler at this point to say that Caldwell does genuinely care about his son, and after hearing about everything Clare went through, Caldwell sees Meg as just another demon to slaughter. (I hope that makes sense.) And I'm so sorry if Jude's 'missing' engagement ring freaked you out. I knew that was going to be a painful part of the chapter, but it had to be written. Lol ;) Thank you guys so much for always reading and reviewing, and thank you for your encouragement with the OCs in this story. I am so happy that you see them as part of the Winchester family, because at this point, I couldn't live without them! :) love you guys! The next chapter will be out soon! :)


	10. Chapter 10

When it came to most things, Castiel's perspective differed drastically from Crowley's. Originating from separate ends of the religious spectrum, the angel and the demon rarely agreed on anything. But despite their varying opinions, Castiel found himself forever in Crowley's debt. If it had not been for Crowley's generous act of transporting Dean to Rufus's cabin all those years ago – allowing Dean to kill Metatron and save Castiel and their newborn son – none of them would be where they were today. Their family would have been hollow and broken without his seemingly uncharacteristic, selfless actions. Castiel owed his very life to the king of Hell.

And that fact made Crowley's slow and painful crawl toward a grisly demise even more painful for Castiel to witness.

The demon was no longer able to speak. The black, plague-like curse had finally reached his throat and had begun to dissolve his vocal chords. Rowena was doing everything in her power to combat the ever-quickening curse; bandaging his body with medicinal herbs, chanting healing spells, assuring him that everything was going to be okay. But Crowley seemed to be in too much pain to even comprehend the help she offered. Though he couldn't speak and his eyes were closed for the most part, Crowley clung to Bobby's hand with an unwavering grip. At this dire point, Bobby was refusing to leave the demon's side, and Castiel understood his reasoning. If – for some unholy reason – _Dean_ had been the one dying slowly and painfully on the couch, and the only help Castiel could offer was simply holding his hand, no manner of heavenly armies could separate the angel from his husband...

“Enough.”

Castiel turned around at the sound of Gabriel's anxious voice. The archangel was looking anywhere but at the blackened demon on the couch, seeming distraught.

“I can't watch this shit get any worse. We need to go gank Death right now,” Gabriel huffed, speaking mostly toward Sam.

“We are, Gabe,” Sam assured comfortingly, “Dean went down to the basement to get the rest of Rowena's supplies and we'll leave as soon as he comes back up.”

“Jessica, dear,” Rowena breathed, brushing some of her own frazzled red hair from her forehead, “Go and help him, would you?”

Jessica nodded once, handed Oliver her things, and got up to sprint passed Castiel to get to the basement. The realization of their impending departure caused Castiel to remember his son and Clarence. The two young men had been avoiding the crowd of their family since their encounter with the warlock. Jude told Castiel, Dean, and Bobby about everything that happened while they were away. And while the thought of Clarence being subjected to the corrupted influence of his father and the sight of his intoxicated mother both hurt and angered Castiel, the angel wanted more than anything to comfort both boys. Unfortunately, he could not comfort them right away, because as Gabriel so painfully pointed out, time was of the essence at the moment...

Wanting to at least inform his son that they were about to leave, Castiel ventured further into Bobby's house to find him and Clarence. The young demon's bedroom was strangely vacant, but luckily, it only took a few minutes of searching for Cas to find the two boys outside on the back porch. Jude and Clarence were perched together on the porch steps as the first few rays of daylight began to shine through the stacks of cars in the distance.

“Jude,” Castiel called quietly.

Both young men turned to look toward Cas and the angel could see hints of emotion on their faces. Had Castiel accidentally interrupted them during a private talk? The angel glanced away shamefully. Perhaps he should have waited a few extra seconds before speaking... Though he was momentarily caught off guard, Jude whispered a small assurance to Clarence and gave him a kiss before climbing up to meet Castiel at the back door.

“Hey, Pop. What's the matter?” he asked.

Castiel attempted to keep his voice very quiet so that he could spare his next words away from Clarence's emotionally-fragile ears.

“Crowley can no longer speak,” the angel informed, staring boldly down into the ocean orbs that mimicked his own, “His health is highly compromised and Rowena has estimated that she can only hold off the curse for a few more hours...”

Jude, of course, took this information with great sorrow. His lips snapped shut and he glanced away with a gulp. Castiel hated to upset his child in this way, but he knew that Jude needed to be informed.

“That is why your father, Gabriel, Sam, and I are leaving immediately,” Cas explained, “We plan to summon and kill Death within the next twenty minutes, and then...”

Though Castiel didn't finish his statement, Jude seemed to understand. Their next course of action was to put an end to the warlock at any cost. Cas wasn't sure how Jude or Clarence would take this information. The warlock was Clarence's father, but he was also an evil man. A man full of hatred and cruel intentions, with no room for compassion. He deserved a fate worse than death, but with time quickly slipping away, all the Winchesters could do was end him as soon as possible. Surprisingly, Jude took the news of the warlock's coming death as a good thing. A brief smile of relief appeared on his lips as he nodded.

“Yeah,” he agreed, “Just do it as fast as you can.”

Castiel was a bit surprised by Jude's sudden willingness to kill Clarence's father. Relieved, of course, but still surprised. Had he spoken to Clarence about this? Was this also how Clarence felt?

“We plan to,” Castiel agreed, glancing toward the demon over his son's shoulder, “How is he, son?”

Jude glanced back toward Clarence as well, who was staring toward the junk cars in the distance.

“His dad messed him up pretty good. Tried to get him to do things that he didn't want to do. Made him think he was bad...” Jude admitted, turning back to Castiel with large, innocent eyes, “Pop?”

“Yes?” Castiel prompted.

Before he spoke again, Jude reached out to wrap both of his arms around Castiel's shoulders. The angel was momentarily confused by his son's sudden affectionate gesture, but quickly hugged him back. Castiel adored holding his child, no matter the time or reason.

“I'm proud to be your son,” Jude whispered sweetly.

A surge of emotion burst through Castiel's chest, causing moisture to rise in his eyes and his heart to flutter. His arms swiftly and tenderly slid tighter around his son's large back, where he held Jude as softly as he did when the boy was only an infant.

“I am proud to be your father,” Cas breathed happily in return.

Jude gave his angelic parent one more tight squeeze before letting go and raising up to meet eyes with him. Castiel gazed at his child with humbleness and appreciation, but also curiosity. Why did Jude feel the urge to voice such a loving statement? Perhaps the events surrounding Clarence and the warlock had stirred his own emotions. Before Castiel could ask his question aloud, Jude turned to walk toward Clarence a few feet away. The angel watched his son kneel next to the upset demon as he backed into Bobby's house to join the rest of their family once more.

On his way back to the study, Cas could feel a twinge of guilt beginning to surface in his own chest. The way Clarence was acting – so confused about his parental lineage and how it effected his current relationships – heavily reminded Castiel of his own husband. From the moment he laid eyes on Dean, Castiel was fully aware of the man's inner turmoil. And seeing Dean as a child, laying in that bed with his little brother back in 1988, made the angel realize just how long Dean had been dealing with the 'demons' that had been passed down from his own father. John Winchester had molded Dean's entire life with his actions. Just as the warlock was molding Clarence's. Just as Edward Thompson molded Oliver's. Just as Castiel had molded Jude's...

All the souls of these men were forged by the care – or lack of care – from their parents.

With this new epiphany swirling in his heart and mind, Castiel reentered the study to find Dean kneeling next to the couch. He had resupplied Rowena and Jessica with the items needed to keep Crowley from being in too much pain, and was now speaking directly to the demon himself.

“Hang in there, Crowley. I've got a few bets riding on you making it out of this,” Dean playfully encouraged.

Though he couldn't speak, Crowley was able to form a faint smile through the grimace of his pain and blinked once. Dean patted Crowley's clinched hand and Bobby's shoulder before standing up and turning to face Castiel, Sam, and Gabriel.

“Let's go,” he prompted.

Castiel quickly reached out to take his husband by the arm and also grabbed onto his own brother. Cas wasn't sure where Gabriel planned to stage Death's murder, but it came as no surprise to him when the archangel flew the four of them back to the diner they were in hours prior. It was the same place they first met Death; a small restaurant that was still closed, due to the extremely early hours of the morning. Upon their arrival, Gabriel instantly walked over to the counter to reassemble the summoning ritual they had left behind. Sam was quick to join him, but Castiel deliberately held Dean back. The angel was anxious to speak to his husband about all the emotions in his heart.

“Dean,” he whispered.

Dean, of course, turned to give Castiel a questioning look.

“Yeah?” he asked.

“I – I'm sorry that you had such a difficult upbringing,” Castiel carefully explained, “It wasn't fair of your father to place his personal burdens on you at such a young age. I understand that you would not be the person you are now if you had not gone through all that suffering, but still doesn't justify what happened -”

“Cas,” Dean interrupted, appearing lost, “Babe, what are you talking about?”

Castiel swallowed the rest of his sentence and could feel a slight sense of panic rising in his awareness. He had to tell Dean what happened. Cas couldn't keep anything from his husband; not when those beautiful jade eyes were so full of worry...

“I visited you, Dean,” he finally admitted, “The other night, I went back in time to 1988... to retrieve the summoning spell to catch the warlock... and I visited you...”

Castiel partially edited the truth to spare Jude and Jessica from Dean's wrath. The angel was expecting to take on all of Dean's anger in that moment. But, to the angel's surprise, Dean only blinked in confusion. The man glanced away in thought before looking back to Castiel in bewilderment. Perhaps Castiel needed to keep talking.

“You were asleep, so I doubt that you remember my presence,” the angel assured, “but seeing you... You were so young, Dean. Too young to be holding a weapon. Your father should have never -”

“Dad?” Dean breathed, eyes suddenly widening with fear, “You saw Dad? Wh – what did he say to you?”

“Nothing,” Castiel answered, glancing away shamefully, “I didn't speak with your father, Dean. I only saw him from a distance. I didn't trust myself enough to get close to him, because I was afraid that I would hurt him... And after seeing you that way, I'm glad I didn't chance it...”

The angel paused to study Dean's reaction, using it to judge whether or not he should continue. Dean seemed a little upset, but still curious. Castiel slowly reached up to cup the side of his husband's warm, freckled face, wanting to comfort him.

“Hey! Love birds!”

Dean and Castiel both flinched out of their deep stare to look to Gabriel.

“Can you postpone the make-out session until later? We're kinda running out of time here,” the archangel grumbled.

Dean coughed before casually turning toward the other men in the room. Castiel was a bit disappointed that their conversation had to be cut short, but he knew that Gabriel was right. Crowley didn't have much time left.

“Okay. Here's the plan,” Gabriel announced, “When Death shows up, we are going to tell him that Dean has chosen to give up his soul -”

“What?!” Castiel instantly gasped.

“Whoa, relax, Cassie. Dean's not actually going to give up his soul,” Gabriel assured, “We just need Death to _think_ that he is so that we can get his scythe.”

“And how, pray tell, are we supposed to get it?” Dean demanded.

Gabriel let out an exhausted sigh.

“Why don't any of you ever pay attention to me when I'm talking?” he groaned, “Death keeps his scythe on his person at all times. The only way we're going to get the damn thing is if Death hands it to us himself. Which means that we have to convince Death that Dean is actually on the chopping block, and then demand that the only way Death can have his soul is if he lets _one of us_ kill him.”

“And instead of using the scythe to kill Dean, we use it on Death instead,” Sam concluded.

Castiel took a very deep breath. As long as Dean wasn't actually in harm's way, he could deal with this dangerous plan. But what if it went astray? What if Death didn't believe them? What if Death caught onto their charade and killed all four of them as repercussion? Cas shared a look with Dean and could see his equal reluctance.

“Alright. I can do that,” Dean carefully admitted, “but who's gonna take out Death?”

“Me,” Gabriel shrugged, “I doubt he'll believe that Sam or Castiel could kill you.”

“That's a good point,” Sam nodded, “Now we just need to make it believable.”

“Exactly,” Gabriel agreed, “which means you guys are going to have to whip up some tears. We've gotta make it look like a funeral parlor in here.”

“Whip up some tears?” Sam nearly scoffed, “Gabe, I can't just cry on command. I'm not -”

Gabriel interrupted Sam's statement by reaching out to tap his glowing fingers against the man's forehead. Sam blinked down at Gabriel several times before letting out a sudden, loud sob. His large eyes swelled with tears and he groaned out with heartache and pain. When Gabriel finally let go of him, Sam spun around to grip Castiel's coat and rest his head on Cas's shoulder.

“What the hell did you just do?” Dean breathed, looking angrily to the archangel responsible for making his brother cry.

“I flooded the link between his amygdala and hypothalamus. He'll be alright. I'll make him feel better later,” Gabe promised, turning his attention to Castiel, “Cassie? You've got to pretend to be angry with me.”

“I _am_ angry with you,” Cas hissed as he pat Sam's large, quivering back.

“Good. Then Death won't see through our plan,” Gabriel nodded, “Alright. I guess it's showtime. Everybody ready?”

No one answered Gabriel. They were all very upset with the way he had haphazardly tossed this plan together. But the archangel took the lack of response as a favorable sign. He turned and began the summoning ritual, repeating the Latin phrase that Castiel had spoken less than twenty-four hours prior. In the meantime, as they waited for Death to appear, Castiel and Dean shared another look with each other. Neither of them agreed with this method of killing Death, but what other choice did they have? It was too late to change the course of events, now. All they could do was go along with the ill-conceived plot and pray that it would work out in their best interest.

After Gabriel's call was sent, the four Winchesters waited quietly in the diner for Death to arrive. Sam was trying his best to keep his sobs to a mere whimper and Cas couldn't help but feel terrible. The angel wished that he had the capacity to sob uncontrollably. Castiel had plenty of reasons to weep – for Clarence, for Crowley, for Dean – but his vessel couldn't display what his grace was feeling. By the time Castiel managed to conjure some moisture in his eyes, Death had already appeared.

The dark figure manifested in the far corner of the room, the only part of the brightly lit diner that had any shade. He lingered in the shadows and observed the scene for a moment before calmly stepping into the center of the room. His cane lightly clacked against the floor with his casual footsteps.

“I take it you've reached a decision,” Death pointed out.

Sam sobbed and quietly tossed his head back down to Castiel's shoulder again. Even Castiel was moved by his acting. Sam was doing a very good job of pretending that Dean was about to be sacrificed.

“Yeah,” Dean answered boldly, “It's me...”

“Excellent,” Death purred smugly, his thin lips curving into a horrid smile.

“But I have some conditions,” Dean quickly added.

Death's smile faded as he stared at the hunter.

“You're in no fit state to be making demands, Dean Winchester,” he hummed coolly, “but I suppose since you are about to meet your demise, I can humor you...”

The dark figure arched an eyebrow to prompt Dean to continue. Dean took a large breath and glanced around at all the other faces in the room with pain.

“Alright. If I'm gonna die, I want to stay dead,” he explained.

“And so you shall,” Death nodded, “I plan to use my scythe to end your life. It will keep your soul from returning to the world of the living... Will that be all?”

“No,” Dean quickly denied, “Gabriel has to be the one who kills me.”

Death very nearly laughed. He shook his head and the sound came out as a weak scoff.

“If you think I would allow that petty child to come anywhere near my weapon, you're sorely mistaken,” Death spoke as if Gabriel wasn't standing three feet away from him.

“Look, I'm not gonna let myself get killed by _you_ ,” Dean denied, firmly shaking his head, “I don't care if my head gets chopped off with a scythe, but someone else has to do it.”

Castiel cringed at Dean's gory depiction, but turned to stare at Death. The dark figure paused to take a large breath and deliberate on Dean's requests. Castiel was very fearful that this plan was on the verge of falling through. Surely Death could see that they were trying to take his scythe from him, couldn't he? Was he merely toying with them at this point? Sam's whimpering was a constant background noise, and it filled Castiel with heartache and dread as he waited for Death's response.

“... Very well,” Death carefully conceded, “I believe Castiel will be a fitting replacement.”

Death's gray eyes slid to stare straight at Castiel and the angel found it hard to draw breath. What? Death wanted Castiel to kill Dean? His own husband?

“Wh – what?” Dean breathed.

“Castiel will kill you,” Death announced, “He will end your life, give your soul to me, and in exchange, I will break my contract with the warlock... Do we have a deal?”

Before anyone in the room could firmly dispute this arrangement, Death opened his hand – and the scythe appeared in his palm. The long, black weapon shimmered in the warm rays of sunlight that stretched in from the windows, reminding the four Winchesters of their true plan. That weapon wasn't going to be used on Dean. It was going to be thrust into Death's unholy body. And Castiel was going to be responsible for delivering the blow...

“You can't make him kill his own husband!” Gabriel shouted angrily.

Death stared forcefully at Castiel with his weapon outstretched, paying no mind to Gabriel's presence at all. The angel purposefully met eyes with his husband, who seemed extremely pained by the news. But Castiel did his best to comfort Dean through their stare alone. After so many long years full of love, Dean knew that Castiel would never hurt him. Perhaps the man was only upset because he feared that it would be difficult for Cas to be put in this situation...

After carefully shifting Sam off of his shoulder, Castiel stepped forward to reach out for the scythe. By now, the tears that had been building in his eyes had finally broke free and were sliding warmly down his cheeks, which was a good thing. Perhaps his tears gave Death the impression that this situation was killing him inside. Cas didn't meet eyes with Death. He only took the weapon from the horseman with a shaky hand and turned to face his most beloved human.

Dean had already knelt down on the floor. He was staring up at Castiel with glistening jade eyes, but there was no fear in them whatsoever. Dean wasn't afraid at all. He trusted Castiel wholeheartedly; even when the angel was holding the single most powerful weapon in the universe. Dean's eyes oozed confidence and trust, and perhaps a bit of encouragement.

“Castiel... You're the love of my life,” Dean whispered, “If I had to pick a way to die, it would be just like this,” he smiled a little, “For our family. With my head held high. Staring up into those beautiful blue eyes of yours...”

Castiel's fingers trembled around the weapon in his hands as he blinked away a few more tears. Though Dean's goodbye wasn't real, Cas could still feel the heartache from it.

“This thing we've got, all this love between you and me,” Dean murmured, gesturing back and forth with his left hand, making his wedding ring sparkle in the morning light, “Death can't touch it. There's not a damn thing that could stop me from loving you, baby... So don't worry. You do what you gotta do, okay? Just remember that no matter what separates us, my heart will always belong to you... I love you, Cas...”

Castiel was not prepared for the tidal wave of emotion that Dean sent his way. Warm liquid was rushing down the angel's cheeks as he gazed down at his husband kneeling on the floor in such a prepared stance. That was such a beautiful and sentimental thing for him to say. How could Dean act out this heart-wrenching scenario so passionately? With Death's eyes still on him, Castiel knew he needed to say something.

“ _I love you, Dean,_ ” Cas replied, his voice cracking perfectly.

Dean nodded and gave Castiel one more look of encouragement before closing his eyes. With Dean prepared, Castiel reared back the large scythe and swung it as forcefully as he could. The angel deliberately missed the top of Dean's head and spun all the way around to plunge the sharp end directly into Death's torso. Death never moved, even when the weapon entered his body. But Castiel forced the curved blade as far as it would go, glaring at the horseman through the blur of his own tears. Though he never said a word, Castiel projected all his blatant wrath through his lethal scowl alone.

To the angel's tremendous surprise, when Death looked down at the scythe in his own body, a calm smile of relief blossomed across his frail lips. When the horseman raised his head, Castiel could see genuine reprieve and gratefulness in his gray eyes.

“Thank you,” Death breathed.

Before Castiel could fully register the phrase, the horseman promptly faded to dust. His entire body collapsed in on itself, floating down to create a soot pile on the floor. Castiel's mouth fell open in shock as he witnessed the phenomenon, and was left holding the most powerful and deadly weapon in the universe.

Against all odds, they had done it. The Winchesters had killed Death itself. But his last sentence was a bit haunting...

“Did – did he just say 'thank you'?” Gabriel broke the silence to ask aloud.

“Yeah, I think he did,” Sam sniffled.

“Wait, did he _want_ us to kill him?” Dean also questioned, rising up from the floor.

“Yeah. Maybe that's why he picked Cas,” Sam suggested as he wiped his own tears away, “He knew Cas would kill him instead of Dean.”

“Well, that's a load of _bullshit_!” Gabriel shouted, “If the bastard wanted to die, why didn't he just ask?! I would have killed him years ago!”

“He _is_ dead, right? He can't come back, can he?” Sam asked.

“Not after being stabbed with that scythe. The dude's dead-dead,” Gabriel reassured, his tone suddenly turning soft, “Come here, moosie. Lemme turn off those waterworks for you.”

Castiel didn't realize how frozen he was until he felt Dean's warm hand on his wrist. The man had stepped over to carefully lower Cas's arms and the weapon with it. Once Castiel turned to fully face his husband, he released the heavy scythe, letting it 'thunk' to the floor next to the pile of ashes. Dean was nodding slowly and wearing a look of understanding.

“It's okay, Cas. It's over,” he promised softly.

No. Dean was wrong. It was most certainly _not_ okay... Feeling his heart on the verge of bursting with sadness, Castiel reached up to wrap his arms tightly around Dean's broad shoulders, holding the man against his own painful chest. Hearing Dean say that loving goodbye had cut the angel to the core. Castiel could never imagine actually having to kill Dean. He could never end his soul mate's life! He would never subject Dean to such a death!

“I – I would never harm you, Dean,” Castiel breathed against the man's ear, “I would never make you say goodbye like that -”

“Shhh, Cas, I know,” Dean replied, his warm hands softly rubbing up and down the length of the angel's back, “I'm sorry I drew it out so long, but I wasn't lying. I meant every word.”

“I know,” Cas nodded, “I could feel it, Dean.”

Instead of replying with words, Dean simply shifted Castiel around in order to capture his mouth with a gentle kiss. It was different from their usually passionate and lustful kisses. This kiss was soft, meaningful, and apologetic; meant as a way of calming the emotional tension between them and restoring peace to Cas's mind. And, of course, it worked. The angel mellowed carefully into his husband's loving embrace. Dean pulled back after a few moments to blink down into Castiel's eyes with a smirk.

“One soulless monster down, and one left to go,” he reminded happily.

 

**Notes for the Chapter:**

> I'm so sorry for all the drama, folks. I really didn't plan to make this chapter so darn feelsy, but it just kinda happened. And I'm also very sorry that I sort of copied the show when it came to Death's death scene. Though, I like to think that I refined it a little, by having Death voice his gratitude for being killed. To me, he didn't really love his job. He seemed kind of stuck doing it, even in the show. So the boys were right in this chapter when they assumed that Death picked Castiel for a reason. Of course he knew that Castiel was going to kill him instead of Dean. (And he figured that Gabriel would have done it just for spite, not actual love, and Death wanted to save himself some dignity there. Lol) To be honest, I think he had his own murder planned out way back when he told the Winchesters he wanted one of their souls. (He knew they would never willingly give up that easy. They're Winchesters!) XD I really hope that I brought his character some justice in his untimely passing. :) Also, I know Castiel and Dean didn't get to have a proper conversation about Cas's trip to the past, but it is coming. ;) We're in the final stretch, dear readers! Thank you so so so much for reading, reviewing, and being generally awesome! :) And I hope that all of you have a wonderful Thanksgiving this week! The thing I'm most thankful for is you! :D The next chapter will be out soon! :)


	11. Chapter 11

The sun was still inching slowly up into the sky, casting bright beams of light through the dew-coated stacks of mangled cars in Bobby's salvage yard, when Jude made his way back to Clarence. The demon glanced up at his fiance, wondering what Cas wanted with him. Clare assumed that Cas told Jude that they were going off to kill Death – a pretty risky, ridiculous, crazy-ass plan, Clare thought – but Jude's chipper attitude suggested otherwise.

“What'd he want?” Clare asked once they were alone again.

“He was just checking on you. He knows how much you've been through,” Jude explained, kneeling back down to Clare's eye level to comb his blonde hair back, “Just like I do.”

Clare couldn't help but close his eyes and indulge in the feeling of Jude's fingers brushing so gently against his scalp. The kid had such tender, loving hands. It still amazed Clare that the same hands that burned an archangel's grace could be so soft and comforting. Jude was such an anomaly; a lethally powerful being who preferred to heal instead of hurt. Someone who would rather save and redeem a wretched soul rather than put it out of its misery. Clarence wished that he could have a single ounce of Jude's compassion and courage. Maybe then, he wouldn't be so damn scared of seeing that warlock again...

“I won't let him hurt you.”

Clare opened his eyes to search Jude's face. Huh. Did Jude just hear everything he was thinking about? Or had they just been together for so long that Jude just knew?

“Get out of my head, Jay,” the demon warned playfully.

The smile on Jude's pretty face made Clarence feel a thousand times better.

“Can't. Sorry,” the kid denied, still raking Clare's hair.

The two of them continued to smile at each other in the morning light, eying each others' lips as if they were considering another kiss, when the back door opened again. Clarence didn't turn around to see who was there. He half expected it to be Jude's other dad, because those guys were always checking to make sure their kid was okay – something that Clarence really admired about their parenting skills. But from the sound of the footsteps alone, Clare could tell that it was more than one person, and that they were probably upset. Clare watched Jude's face, seeing him look up with a hint of sadness.

“Jessie? Are you okay?” he asked.

Before she answered, Jessica led her red-haired boyfriend toward the stairs. She and Oliver nestled themselves next to Clare and Jude on the stairs, burrowing into their space without so much as asking. Clare was a little bummed that his and Jude's alone time was over, but seeing the moist lines on Jess's face from where she had been crying made him reconsider. Neither of the new arrivals said anything at first. They just sat down and stared blankly toward the salvage yard. But Oliver seemed to be able to talk before Jess. The ginger reached out to give Clare's back a single, manly pat.

“Sorry about your dad, Clare,” he offered.

The remembrance of the warlock made Clarence feel sick to his stomach. He appreciated Oliver's sympathy, but he hated that the guy had to bring it back up...

“Yeah,” Clare huffed, “I'm sorry the warlock's an asshole, too.”

Oliver's hand slipped off Clare's back and his eyebrows scrunched with confusion.

“Uh, n – no,” he stuttered, “I meant Crowley. I'm sorry he's in pain...”

Clarence blinked hard at the redhead on the steps next to him. Oliver wasn't trying to be funny. The kid was being absolutely genuine. Oliver referred to Crowley as Clare's dad purposefully, as if he always saw them as father and son. As soon as the realization set in, Clarence tilted his head away to think about it. Holy shit. Crowley _was_ kind of like his dad, wasn't he? Granted, they had never tossed a baseball back and forth, or did any of that other mushy stereotypical bullshit... but Crowley _did_ teach Clare all about demon-kind. He let Clarence come to Hell whenever he wanted, gave him his own hellhound, and even let him sit on the throne once. Crowley always gave Clare sound advice and treated him like an equal. Bobby filled the role of Clare's caretaker, but Crowley was his wing man; forever getting him into and out of trouble. Crowley even helped Clare pick out the engagement ring he gave to Jude...

Crowley really was Clare's dad.

And thinking about the state Crowley was in now devastated Clare. He hated the thought of Crowley suffering in the study, slowly dying in a painful way. In fact, it made Clarence hate the warlock even more. Caldwell could probably break that curse with the snap of his fingers or something, but he would rather let Crowley die a painful death than to lift his hand to help a demon. The asshole...

“Do you guys have any idea where the warlock is?” Jessica asked softly.

Jude shook his head.

“The last time we saw him, he fell on his own blade and disappeared,” he said.

“Well, we need to figure out where he is so we can kill him once and for all. Is there some way we can track him?” Jess continued to brainstorm.

“Well, I know how to summon him. But that didn't work out so well last time,” Oliver mentioned bashfully.

“Yeah, let's not do that again,” Jude agreed.

“Do you think he'll be easier to kill after Death is dead?” Oliver asked, “I mean, he's still a magician. Might be hard to fight.”

“It's all of us against him,” Jessica pointed out, “We have a team and he's alone. I think we can take him.”

“That's what everyone thought when you guys tried to take him at the lounge, remember?” Jude hesitantly reminded.

“Yeah, but we didn't know what we were up against then. Now, we know,” Jessica said, sitting up a little straighter, “We should come up with a plan.”

“A plan? What, are you gonna try to fight the guy without your parents?” Clare huffed.

“Yes,” Jessica answered with a nod, “Crowley is running out of time. I'm not going to let him die because of that jerk, Clare.”

Clarence gulped, feeling slightly proud. It was nice to hear the determination in Jess's voice. She was usually too emotional when it came to confronting things head on, but her love for Crowley must have changed that...

“Oliver's right, the warlock might be tough to take down because he's got magic,” Jessica recalled, her eyes quizzical as she thought, “If we had a way to distract him, it would make it easier for us to get close enough to strike. Clare, does he have a weakness?”

Clarence took a deep breath and forced himself to think back to the time he was alone with Caldwell in that crack house. The guy seemed to have everything under control the whole time. He had hundreds of years of magical expertise. There was no way he had a weakness when it came to magic.

“I don't think so...” the demon reluctantly denied.

“Yes, he does.”

Clarence looked up at Jude, who had spoken calmly. The blue-eyed angel was smiling at Clare, looking all around his face with warmth... and what seemed like a twinge of mischief. But Clare was lost.

“It's you,” Jude explained, reaching up to brush his fingertips over the demon's cheek, “Clare, the warlock's weakness is _you_.”

Clarence's jaw nearly hit the wooden steps of the porch. Shit, Jude was right. The warlock had already died twice, and both times were because he was so focused on Clarence that he didn't even think about other people swooping in to harm him. Clare really was Caldwell's weakness... While everyone considered Jude's statement, Clare noticed that Jessica was staring hard at the crushed cars in the distance. She blinked at a particular stack of rusted metal and an eager, proud smile slowly bloomed on her face in the morning sun.

“I think I've got a plan,” she smirked.

* * *

Clare could feel his hand shaking inside Jude's as they waited for Oliver to flip to a certain page in a spell book. The three of them were standing in an aisle between two lines of mangled cars on the edge of Bobby's salvage yard, far enough away so that the house could barely be seen in the distance. Jessica was close by too, perched high up on top of a stack of cars, looking down at them with a bird's eye view. Being able to see from that angle was part of her plan. Though, it was a plan that Clare wasn't too fond of... because it involved him having to speak to the warlock again.

“Do I have to talk to him?” Clare breathed.

Jude's hand instantly squeezed the demon's fingers.

“It's okay, Clare. I'll be right here with you the whole time,” he promised sweetly.

Clare huffed a breath of discomfort. He didn't like the thought of Caldwell being close to Jude, either. But at this point, what choice did they have? Dean, Sam, and the other guys were out there – hopefully – killing Death, and Bobby and Rowena were busy keeping Crowley alive. Clare, Jude, Oliver, and Jessica were the only ones left that could put the warlock down. Still, Clare would have given anything for someone else to take over his place, because he couldn't stand the thought of seeing the bastard again. What if he tried that sweet-talk shit? What if he tried to persuade one of them to turn against the others? What if he used his magic to manipulate someone? What if he wouldn't die? What if they ambushed him and someone got hurt? There were so many ways this could go wrong...

“Here it is,” Oliver smiled at last, “This is the spell thing I said earlier that made the warlock show up in the garage. You know, right before he threw me and Sam in Hell -”

“We remember, Ollie,” Jessica's voice echoed from somewhere overhead to interrupt, “Just say it and get the heck out of there.”

Oliver glanced up and looked around, probably searching for his girlfriend who was well hidden out of sight, before doing what he was told. The freckle-faced kid started reciting the Latin paragraph – rather badly, Clare noticed. Rowena would have corrected him several times over, if she was there to hear him say it – and raised his head every so often to see if it was working. Clarence, on the other hand, was trying hard just to keep his own eyes from closing. His stomach was in knots, his heart was pounding, and he felt like throwing up. Ugh, he did _not_ want to see the warlock again. After everything that bastard put him through – especially with Meg and that crack house – Clarence was pretty much done with Caldwell. Biological father or not, the guy was sick and twisted. Clare wasn't sure which part he was more afraid of; being forced to see his real father again, or finding out more similarities between them.

“I'm right here, Clare,” Jude's soft voice reminded again, warm breath brushing against the demon's ear, “No one's going to hurt you while I'm around.”

With his fiance's protective tone ringing in his mind, Clarence found the courage to keep his head up. Jude smiled a little at him as the two of them listened to Oliver butcher the Latin language. But just when Clare started to get his own emotions under control...

“Clarence?”

The eerily hopeful voice was enough to make chills inch across the demon's skin. Oh, God. It worked. The warlock was in the salvage yard... Oliver paused his recital of the Latin to turn around and look behind them with a gulp. Jude turned around next, to glare at the bastard with the fiercest scowl Clare had ever seen on his sweet face. But Clare, the main focus of the warlock's attention, was momentarily paralyzed with fear. ' _Don't turn around. Don't look at him_ ,' the voice in his head begged. But even though he was terrified, Clare knew he had to face him and look him in the eye. The demon drew his fingers tight around his angel's hand before forcing himself to slowly spin.

The warlock was standing calmly at the end of the lane, positioned perfectly between the stacks of rusted vehicles. Of course, his reddish eyes were zeroed in on Clarence, and it made the demon extremely uncomfortable. Caldwell was back from the dead again, looking more lively than ever. It made Clarence want to puke...

“Son,” the guy muttered, “I... I'm surprised that you actually summoned me. Our last meeting didn't go as well as I'd hoped. I figured you'd never want to see me again...”

Everything in Clare's body wanted him to open his mouth and tell the bastard that he was right, but he didn't. The demon kept the truth behind his sealed lips. In the small silence that followed, the warlock briefly glanced toward the other two men at each of Clare's sides with caution.

“Are these brutes really your friends?” the warlock asked, sounding exasperated as he looked to Oliver, “Be careful around that ginger, Clarence. He'll chuck bricks at your head for sport... and _that_ one,” he said, shaking his head toward Jude but looking at him quizzically, “I realize that he's important to you, but I'm still not sure how. Is he... your best friend or something?”

“Yes,” Clarence instantly agreed, tugging on Jude's hand a bit, “and my fiance.”

A skewed, bizarre look came across the warlock's face, making the long scar on his cheek twist oddly. He was smiling, but his eyes were narrowed, as if he thought that Clare had said an offensive joke. The guy let out a small, hollow chuckle and shook his head as he took a tiny step closer to the three other men.

“I – I'm sorry, I must have misheard you,” Caldwell murmured smoothly, “Did you say -?”

“Future husband,” Jude repeated firmly, casually shifting around to stand slightly in front of Clare.

The humor dimmed on Caldwell's face. He managed to hold onto a faint smile, but it was turning morbid. Creepy, even. The warlock's eyes eventually aimed straight toward Clarence and the demon felt terrified.

“Y – you're a queer?” the warlock breathed, voice vile and growling as he shook his head back and forth, “Tell me you're joking, Clarence. Tell me it isn't true... All of this work... All this effort I've put into getting to know you... and you've been a _faggot_ the whole damn time?”

Clarence's blood ran cold in his veins. His eyes, starting to flood with tears, were frozen; locked on the hateful man in front of him. There was a time that being called those cruel names didn't even affect Clare. But when it was said like _that_ – like the entire two days the warlock spent trying to get to know Clare was meaningless just because he was in love with a man – rocked the foundation of his being. What an absolute dickhead. It was too bad Clarence couldn't feel his body at the moment, because he would have flipped the asshole his middle finger and spit toward him.

Thankfully, Caldwell's harsh statement wasn't taken so lightly by anyone else. Oliver tossed the book in his hand to the dirt and clinched his fists with his head down, as if he was planning to charge toward the warlock like a bull targeting the color red. Jude lit up like a Christmas tree; eyes and skin glowing bright with grace, so much that Clarence could almost feel his fingers burning before Jude let go of his hand.

“What the hell did you just call him?” Oliver barked.

Clarence was genuinely surprised that Jess's calm, polite – and very _human_ – boyfriend was taking up for him. Especially when the bully was an extremely old, extremely powerful magician. Oliver had balls, Clare had to give him that. But the poor redhead was probably no match for the warlock. Jude and Jessica, on the other hand, seemed to be the most dangerous beings present.

As if on cue, a golden blast exploded behind a stack of cars. According to plan, Jessica had used her grace to push over a tower of smashed vehicles, sending them toppling toward the middle of the aisle, where the warlock was standing. Caldwell barely had enough time to look up and see the metal stack falling toward him before he was buried under the mechanical rubble. Jude, Oliver, and Clarence all stepped back and shielded their eyes to keep them safe from flying glass and debris. The loud, colossal crash of the cars falling made the ground tremble a little, and Clare could almost feel the impact in his chest. There was no way the warlock could have dodged that one.

Still, once the dust cleared, Jessica dashed over from behind her hiding spot to rejoin the boys in looking at the destruction. The old crushed cars had filled most of the aisle, making the salvage yard look more like a war zone. Clarence was determined to find out of the warlock was really dead this time. The last thing he wanted was for that bastard to show his scarred face again.

“Did we get him?” Oliver asked.

“I think so,” Jess answered, “Jude, help me lift up some of these cars so we can look underneath.”

Jude paused to turn and give Clare a reassuring look before following his cousin to the mess they made. Clarence stood next to Oliver and watched the angels shift the hulking cars around like they were made of plastic rather than compressed metal. Clarence didn't realize that his fingers were tapping nervously against his jeans until he looked down and saw them moving. God, he wanted the warlock dead so bad. He wanted it to be over, once and for all.

A flash of black smoke suddenly burst around Clarence.

The demon barely had time to look up and see Jude, Jess, and Oliver before the smoke surrounded him completely. It began to dissipate the moment it clouded over, but revealed an entirely new setting. Clarence was only able to glance around and see that he was inside some kind of shelter before he was thrown against a wall. He stumbled against the flat surface and gasped, feeling a pair of hands spin him around and cover his mouth. Clarence blinked in fear, staring at the warlock he had been so desperate to get rid of.

“Nice try, _son_ ,” Caldwell hissed, his voice filled with betrayal and anger, “You and your little friends failed. Again. That seems to be the theme of your life, doesn't it?”

Clarence tried his best to fight against the warlock's hold, kicking and shoving, trying to get away – but he stopped short when a shiny black blade flashed up into the light.

“Ah, ah, ah,” the warlock said, shaking his head as he swished the blade in the air in a disapproving fashion, “There's no point in struggling now... I had such high hopes for you, Clarence,” he grumbled, his voice dropping to a mournful tone, “I hoped that my influence would change you for the better. That we could take on the rest of the world together... but it turns out that you are just like that worthless, demonic whore I impregnated. You're a sinful, diseased, arrogant, wretched demon. Just like the rest... And now, it's time for me to put you where you belong.”

The blade raised up high in the light and Clarence started to panic. Oh shit! The bastard was going to kill him! Clarence's mouth was still covered with the warlock's free hand, so he couldn't pray to Jude out loud – but that didn't stop him from screaming the guy's name in his mind. Jude's name was on an endless loop in Clare's head; _Jude! Jude! Jude!_

Just before the blade swooped down toward Clare, a large blast of light flashed through the room. Clarence closed his eyes and tilted his head away, feeling the warlock finally let go of him. Clare gasped for air and dropped to the floor, where he crawled away as quickly as possible. He had no idea where he was. All he knew was that he had to get as far away from the warlock as possible.

“Clare!”

The demon paused to look toward the sound of Jude's voice. Holy shit, Jude actually heard him! The guy had flown to their location somehow, and was now fighting with Caldwell. The angel was currently playing defense; dodging various sharp weapons that the warlock threw at him. Jude was able to get a good blast of grace in, but the warlock was quick to recoil. He sprang up, said a string of odd words, and flicked his hands together, which caused the walls of the room to slide together. Everything was suddenly compressed between the walls that were only a few feet apart, now, leaving almost no room for Clare to hide in.

Seemingly just in time, a new flash of light erupted in the room. This light was golden, and was followed by a cascade of feathery blonde hair. Clare focused his eyes toward the left side of the room, where Jessica and Oliver had both appeared. Oliver dashed over to kneel next to Clare, but Jess joined Jude in the fight. The walls had slid back into their original positions, giving them the room they needed to battle. A few scuffles ensued before the blonde girl popped herself closer to the warlock, grabbed him by the collar, and body slammed him to the floor. She pinned him there and reared back to give him a solid, audible right hook.

“That was for Crowley,” she barked.

The angel raised her solid fist to punch the asshole in the face again, bashing the back of his head against the floor in the process.

“That was for Clare,” she growled.

Then, Jessica positioned her glowing hand right over the center of the warlock's chest. The guy was so woozy from her previous punches that he could barely hold his head up to see what she was doing. But Jessica narrowed her eyes toward Caldwell's face anyway.

“And this,” she hissed, “this is for all the women you've raped and killed.”

Before the warlock could even look down, Jessica used her grace to blast a hole right through his chest. The solid beam of light was so strong that Clarence had to look away to keep from hurting his eyes. It lasted a few long, glorious seconds before fading away with the warlock's scream. After the devastating blast was fully delivered, there was only silence and the panting of breath. Clare finally raised his head to look around and see what happened. Jude and Oliver were kneeling on the floor next to him, but Jessica was still hunched over the warlock. He was dead – a gaping, bloody hole left where his heart was supposed to be – but Jessica didn't move. She stayed put and glared at his corpse, as if she was daring it to disappear. The boys stared at the warlock's dead body too, all wondering the same thing. Was he really going to stay dead, this time? Was his contract with Death still in effect, or did they manage to kill him after it was voided by Dean and the others?

One minute turned into two, two turned into three. Ten minutes later, Clare and his friends were still blinking toward the warlock in suspicion, waiting for him to fade away. But he never did. Caldwell's eyes were empty, vacantly cast toward the ceiling. Lifeless. It seemed like the Winchesters had finally done it. The warlock was finally dead. And that meant -

“Crowley,” Clarence eventually found his voice to say.

Saying his name seemed to be enough to move everyone else into action. Jessica, Jude, and Oliver all glanced toward each other before scurrying over to group together. They all took one last look at the warlock, making sure he was _really_ dead, before flying away. Clarence closed his eyes and braced against Jude for the ride. He had no idea where the warlock had taken him, so he didn't know how long it would take them to show back up at Bobby's. But they were there in the blink of an eye, standing in the hallway that led to the kitchen and study. The moment they arrived, Clare could hear the voices of Jude and Jess's parents coming from the study.

“ - must have killed him somehow,” Dean said.

“But where are they, Dean? Where are the children? And how could they have managed to kill the warlock by themselves?”

“They're not children, Cassie. How many times do we have to tell you that?” Gabe grumbled.

“Can you morons stop arguing for five bloody minutes? I've barely had time to catch my breath and you're already at each other,” Crowley's voice hissed.

Clare's mouth fell open as he shared glances with his friends in the hall. Crowley was speaking! His voice was back! Was the curse broken? Without a word, all four of them raced into the study to see the rest of their family. Clarence was in the back of the group, but that didn't stop him from craning his neck to see the couch. There, hunching on the sofa like a tired old man, Crowley was sitting up and taking deep breaths. His shirt was still off, but his body looked completely intact. The black goo was gone and his skin was smooth again. Crowley wasn't dying anymore. He was perfectly fine, back to his old sassy self.

The moment Jess, Oliver, Jude, and Clarence stepped into the room, everyone swarmed each other with embraces. Choruses of “There you are!” and “You did it!” filled the room, along with cheerful shouts of names. Bobby was the first one to hug Clare. The big guy rushed through the crowd, sighed with relief, and tossed both of his large arms around the demon's shoulders. Clarence even got a small hug from Castiel too, who seemed very pleased to see him in one piece. But most of Clare's attention was on Crowley. Jude and Jessica had already gone over to give him proper hugs and Bobby walked back over to sit with him. Eventually, Clare and Crowley met eyes in the crowd and a faint smile lifted on Crowley's face. Neither of them seemed to know what to say, but it didn't matter. Clare was just overjoyed to see Crowley – his real father – safe and happy again.

Clare shifted around the rest of the Winchesters to get across the study, where he plopped himself on the couch next to Bobby and Crowley to wrap an arm around the king of Hell. Crowley sighed and patted Clare's arm in return.

“I'm glad you're okay, boy,” the British demon hummed, only for Clare to hear,“I don't say this very often, but... I'm sorry... I should have told you about that maniac sooner.”

Clare only blinked at the demon king in confusion. Sorry? Crowley didn't have a damn thing to be sorry for. The guy was a saint compared to the warlock.

“It's fine,” Clare replied warmly, smiling as brightly as he could, “I'm just glad you're okay, because Jude and I still need you to usher for our wedding -”

“Ah, yes, indeed,” Crowley smiled and winked, playing along with the joke.

The two demons grinned at each other before sliding into one last embrace. In that moment, as he hugged the newly restored king of Hell, Clarence felt the emotional weight of the past few days tugging on his heart. Having Bobby and Crowley around meant so much to him, and he couldn't deny the urge to let them know it.

“Hey. Thanks for taking me in,” Clare breathed, backing up to look between the demon and the old hunter, “I know I wasn't the nicest teenager, but -”

“Nonsense,” Crowley interrupted, his accent as smooth as silk, “Everyone is a bit rough around the edges. But you, my dear boy, are one of the greatest treasures in our lives. I consider myself lucky just to... to call you _son_.”

“He's right,” Bobby nodded in agreement, giving Clare a wise look from under the bill of his hat, “Family don't end in blood, boy. And it don't start with it either. You're a part of this family, no matter what anyone else says, you hear me?”

Clare gulped and nodded, looking between the two men on the couch as he felt the broken pieces of his heart slowly mending back together. It was such a welcome change to be considered part of the family. That was the biggest distinction between the warlock and the Singers; the fact that one wanted him to be a certain way, and the other wanted him just as he was...

A loud, winded, dramatic sigh came from across the room and almost everyone turned toward the kitchen. Rowena – red hair tossed in all directions, fancy dress stained with various oils and potions, sleeves rolled up, hands and face dirty, and eyes weary and dark from lack of sleep – had slumped into the nearest kitchen chair and was blinking back at the crowd. Though she was extremely exhausted and looked like she could use a hot bath, she still managed to smile back at the rest of them.

“I s'pose it's official,” she hummed, “No Death, nor magic, could tear this family apart.”

 

**Notes for the Chapter:**

> Ahh, finally. I think we can all breathe a little better now that the warlock is gone. Especially Clare. ;) I know that his sudden turn on Clare might have seemed a little abrupt, but Caldwell genuinely had no idea that Clare was going to marry Jude. And he was not on board with the homosexual lifestyle. (Sound like Eddie Thompson, much? Lol) ;) And I couldn't help but give that final kill to Jessica, because after everything he did, the warlock deserved to die by a woman's hand. Plus, Jessie really needed that kill. She blamed herself for what happened to Crowley, and now she feels like she righted a wrong. :) I promise that the warlock is offically dead. We won't have to see or hear from him ever again. :) And yay! Crowley is back! The old sass master is safe and sound. ;) I really hope you all enjoyed the chapter! Thank you so much for reading and commenting! The next chapter will be out soon! :)


	12. Chapter 12

“Well... I've gotta hand it to my baby rabbit,” Gabe sighed as he blinked down at the warlock's corpse, nudging the dead guy's arm with his foot, “She really knows how to make someone dead.”

Though he didn't say anything, Dean silently agreed with the archangel. Not only was a huge chunk of the warlock's chest missing, but the edges of the perfectly circular wound had been burned; as if a solid beam of light had vaporized everything inside the blast area. Dean was proud of his niece for being able to deliver the final blow, but the part that disturbed him was the fact that the monster's lifeless face looked too much like Clarence's...

After everyone had their reunion in Bobby's study, they immediately swapped stories. Dean and the others told the kids about their showdown – more like _letdown_ – with Death, and the kids told their parents everything that happened with the warlock. Dean was pretty impressed by how well Jess and the boys handled the bastard on their own. He honestly didn't think that the kids would be able to take on the warlock by themselves, especially since Clarence seemed confused with the whole 'dad' thing. But Crowley's broken curse and the warlock's dead body were enough to make Dean eat crow.

With everyone back together and safe, the Winchesters weren't sure what to do next. That is, until Sam suggested that Caldwell's body needed to be salted and burned. Dean wholeheartedly agreed with his little brother. They need to make sure that the warlock was going to _stay_ dead; No more of this 'popping up unexpectedly' crap. Rowena requested to stay behind and nap – something she desperately needed and rightfully deserved – but Jessica and Jude agreed to fly their parents and uncles back to the shelter they came from so that they could commence with the burning ritual. Dean wasn't sure where exactly on the globe the place was located, but the room itself reminded him of some kind of tiny warehouse. It was one room, with high ceilings, metal walls and rafters, not many windows, and a chilly atmosphere. From the paper-cluttered tables, shelves of old books, stacks of caldrons, weird spices hanging from the ceiling, and mounted animal heads, Dean assumed that this must have been where the warlock lived.

When they arrived, everyone stole at least one glance at the dead body on the floor. It was on its back, blandly facing the ceiling, arms and legs limp. Luckily, there were no bad smells yet. Just the faint whiff of singed cloth and burned wood. The kids immediately shifted to the vacant side of the room while Dean, Cas, Sam, and Gabe converged on the corpse. In the meantime, Bobby and Crowley started looking around at all of the books, papers, potions, and items in the house, probably looking for anything they could salvage and make use of.

“Should we burn it in here? Or take it outside?” Sam asked quietly, probably keeping his voice down so that Clarence couldn't hear it.

“Outside. Unless...” Dean trailed off, glancing around, “Should we burn the whole place down with it?”

“Yes.”

Dean turned to look at Crowley, who was looking inside of an old leather-bound book. He snapped it shut and held it up, wearing an angered expression as he pointed toward a whole row of similar books on the shelf behind him.

“Journals. Detailing the time he spent with each of his victims,” Crowley explained, looking like he was trying to suppress a fit of rage, “Hundreds of years worth of plotted murder and lustful filth. Documented misogyny... It all needs to burn.”

Dean's stomach turned sour as he looked along the rows of tattered books behind Crowley. Holy shit, there had to be at least fifty of them or more. How many victims were in each book? How many names and descriptions? How many lines of handwritten text reciting the sexual torture and heartless murder of demonic women? _And which one of them included Meg's story_? Before Dean could even open his mouth to say anything, Bobby struck a lighter and tossed it onto the shelf. The flames slowly caught onto the spine of a book and spread to catch the rest. Within the first few seconds, the whole row was engulfed, destroying every word the warlock ever wrote. It was for the best. No one needed to delve any deeper into the madman's mind.

With the house beginning to burn around them, Bobby and Gabriel took the liberty of escorting the kids outside. The gathering smoke was making it difficult to breathe, but Dean, Sam, Cas, and Crowley stayed inside long enough to coat the warlock's corpse with salt and make sure it would catch fire too. Dean would have been lying if he said that seeing the bastard burn wasn't satisfying. After everything the warlock put the Winchesters through during the past few days – and even long before they even knew him – it was finally over. Dean stood inside the blazing house and stared at the destruction for as long as he could before Cas started to tug him toward the door. The man covered his mouth and finally tore his eyes away from Caldwell's blackened body before ducking out of the house behind his husband.

The first thing Dean saw when he opened his eyes outside was the color green. Lush, rolling emerald hills were all around the burning house, beautifully contrasted against the overcast sky and the deep blue ocean in the far distance. After only a few glances, Dean was sure that he was somewhere in Europe. Granted, he didn't have any experience with being out of the states, but he had watched enough TV to recognize the strikingly green fields. Plus, the distant cliff that greeted the ocean seemed familiarly foreign, too.

Apart from the signature grassland, Dean noticed that the rest of his family was situated off to the side. They were staring toward the bottom of the hill, where some kind of overgrown ruin was barely sticking out of the ground. Dean shared a small, curious glance with Cas before wandering over to see what it was. The closer he got to the group, the more Dean could recognize the outline of a building. It seemed like an old foundation of a house, but it was buried under mounds of weeds and grass. It had to have been sitting there collecting foliage for at least a few centuries. But, why was everyone staring at it? What made it so special?

It wasn't until Dean looked around again and noticed that Jude and Clare were separated from the group that he began to pick up hints. The boys were staring down at two large, gray things jutting out of the ground. Still curious, Dean stuffed his hands into his pockets and slowly made his way over to see what had their attention. Once he was close enough, Dean could see that the boys were looking at two stones, each with one word carved into it. The chisel job was bad, like it was written by a child. Though he could barely make it out, Dean saw that one stone said 'Father' and the other said, 'Mother.' The man searched between the two stones and slowly realized – these were the graves of the warlock's parents. That overgrown ruin behind them was a destroyed farmhouse. It was _real_. The entire story the warlock told Clarence about his life was _true_. And that meant the two graves in front of them belonged to Clarence's actual grandparents...

For a second, Dean, Jude, and Clarence all stood there and blinked down at the makeshift headstones in silence. Dean didn't know what to say, and it seemed like Jude didn't either. They just huddled around Clare, offering him support by just being present. A cool breeze rolled over the hill, ruffling the grass, their hair, and clothes, and seemed to stir Clarence from his daze.

“Jay,” he muttered.

“Yeah?” Jude instantly replied, turning to look at the demon properly.

“Can you give me a minute alone with your dad?” Clare asked.

Dean gulped and shared a small look of surprise with his son. Whoa, Clare wanted to talk to Dean? Alone? Dean always thought that the demon preferred Jude's company and conversation to anyone else's, but maybe the kid needed a different kind of support right now. Jude nodded, leaned over to sneak a small peck to Clare's cheekbone, and squeezed his hand before walking back to the rest of the group. Dean gave his son a shrug of confusion as he passed by, to which Jude shrugged too. Clearly, Jude didn't know why Clare wanted to talk to him either. Still, Dean remained close to the blonde kid and even stepped a little closer. More time drifted by, in which Clare stared blankly at the two headstones before speaking.

“Dean,” he muttered, his voice barely audible against the Celtic breeze, “You've killed a lot of people, right?”

Dean was sort of caught off guard. Wow, that was a heavy question. But he wanted to be honest.

“Yeah, kid. I have,” the man answered.

When it came to hunting, people died all the time. And Dean couldn't deny that there had been a lot of folks at the wrong end of his weapon. Probably too many. Clare was quiet for another moment, barely moving as the wind tossed his blonde hair around.

“Does killing them make you feel better?” he asked, still staring at the stones, “When they're bad, I mean. When they deserve it... Does it make you feel better when they die?”

Dean gulped.

“... No,” the man breathed truthfully, shaking his head as he recalled all the corpses he had to burn in the past, “Not a damn bit. I always feel worse, somehow.”

Clare nodded a little and shifted around, rocking back on his feet. He tilted his head toward Dean but didn't look directly at him.

“He told me it would,” the demon said, obviously referring to the warlock, “He said I would feel better if I killed Meg. Like all that shit she put me through would go away or something... but I... I don't think it would've changed anything...”

“It wouldn't,” Dean agreed, “What's done is done. Killing the person responsible for ruining your life won't change what's already happened.”

Though he seemed to agree with Dean's statement, Clare didn't appear very moved by it. He just nodded blandly and blinked at the headstones. Dean knew what the kid needed. Clare needed a revelation; a solid, genuine answer to all the questions that had been stirred up in his mind lately. And, for Dean, there was always one place to get that kind of understanding... and that was from his husband.

“Clare, I... I won't stand here and preach to you. I'm not very good at it, anyway,” he began carefully, “but I've been married to an angel for a couple of decades now, and he's taught me a lot about – well, about everything.”

Clarence finally turned to look fully at Dean, probably because he was eager to hear about being in a long term relationship with an angel.

“One of the things I've learned is that it's easy to get trapped in a revolving door of anger and blame,” Dean continued, hoping his words made sense, “You chase after who you think is responsible for your troubles, and when that doesn't pan out, you look for someone or something else to blame. You feel like _someone_ has to pay. Someone _owes_ you something, because what you went through took time away from your life – time you can't get back. And it isn't fair... but what you don't realize, is that all that time you spent running in circles eats away at your life, too. It all adds up. Believe me, I've been there. It's not a pretty cycle...” Dean paused to shake his head and take a deep breath, stealing a glance toward Cas a few yards away, “but there _is_ a way to break it.”

“How?” Clarence blurted, staring so hard at Dean that his eyes were starting to water.

Dean let out a breathless chuckle.

“You're probably not gonna believe me when I say this,” he mumbled, “but... You forgive them.”

Clare's expression shifted like he was going to grimace, but Dean held up his hand in defense.

“I know. It sounds stupid, right?” Dean smiled, scratching the back of his head, “For the longest time, I thought it was a load of bullshit. But then, my saint of a husband explained it to me, and it made perfect sense... Forgiveness doesn't excuse what that person did to you. It just helps you break out of that damn circle. It helps you release all that weight and anger you've been carrying around, and makes you feel a million times better... And, hey, if you still want revenge, you know what you should do?”

“What?” Clare breathed.

“Marry my son,” Dean answered, letting a smile spread on his lips, “Fix up old cars with Bobby. Help Crowley run things in Hell. Let Rowena pamper the shit out of you. Hang out with the kids. Hang out with us. Live your life the way you want. _Be happy_ ,” he emphasized with a nod, “Trust me, kid. That's the sweetest revenge you'll ever taste.”

After those words, Dean paused to see if they were going to take effect on Clare. The hunter was glad to see the tiny smile trying to work its way across the demon's face. It was faint and weak, but definitely visible.

“Thanks,” Clare muttered, his voice timid but honest.

“Anytime,” Dean offered with a wink, “C'mon. You know Jude's worried sick about you.”

Clare smirked and nodded – agreeing that Dean's son had probably been watching them closely the entire time – and followed Dean back toward the group. As he walked, Dean noticed that smoke was billowing up into the sky from the house in the distance, getting larger and darker as the fire spread. The Winchesters seemed to be waiting for him and Clare to return so that the angels could fly them all back home. Jude, of course, welcomed Clarence with open arms and a warm smile. And while Cas's arms weren't open for Dean, the man could tell that his husband was just as excited to see him. Dean smiled at the blue-eyed angel as he sauntered up. Did Cas hear any of that conversation he had with Clare? Did Cas know that Dean saw him as his main source of truth, understanding, wisdom, and love? That little twinkle in the guy's sapphire eyes seemed to say yes.

“You know, Moose, when I said I wanted to take the family on a trip to Europe, this is not what I had in mind,” Gabriel muttered from the side, “I can't wait to get out of here. Carry me home.”

“Gabe, _you're_ the one with the wings. You carry _us_ home,” Sam instructed.

“Oooh. I love it when you get all demanding,” Gabe purred, nestling against Sam's side.

Dean was expecting Bobby or Crowley to spit an annoyed comment at Gabriel for being gross, but the two elder men only smiled and shared a glance with each other. Luckily, Jessica seemed disturbed enough to say something. She tucked her red face behind Oliver's shoulder and grimaced.

“Can we just go now, please?” she called.

The angels started reaching out for various family members and disappearing; flying everyone back to Bobby's house to regroup. Gabe took Sam and Bobby, Jessica took Crowley and Oliver, and Jude closed his eyes and slowly took Clare. Dean and Cas were the last ones standing in the breezy, emerald field, and Dean was kind of glad. He had been meaning to say a few words to his husband alone. As Cas reached up, Dean lifted his hand to tangle their fingers together.

“Hey, wait a second,” Dean requested softly, bringing his hand down to hold.

The hidden smile on Cas's face vanished and was replaced with concern.

“What's the matter, Dean? Was your conversation with Clarence upsetting?” the angel attempted to understand.

“No. It was fine,” Dean corrected, searching the angel's entire pretty face, “It's just... you said you went back in time and visited me, right?”

A blush slowly appeared on Cas's cheeks. The cool breeze tossed around some of his raven hair, revealing even more of his timid features.

“Yes,” he admitted quietly.

Dean smirked a little. Maybe Cas thought Dean would be upset with him for going back in time to see him, but it couldn't have been farther from the truth.

“You gave me that dream about Mom, didn't you?” Dean guessed.

Cas's mouth fell open. His blue eyes widened a bit and he searched Dean's face in astonishment.

“H – How... How did you know that I – ?” Cas gulped, “Y – You were asleep, Dean. How did you know I gave you that dream?”

The confirmation that it was true only made Dean smile more.

“'Cause, when I was a kid, every dream I had about Mom was a nightmare,” he explained, briefly recalling all the times he was forced to rewatch her burn on the ceiling in his sleep, “I used to be so scared to go to sleep, sometimes I would stay up and watch Sam... But that night... It was the first time I dreamed about her being alive and happy. We were playing tag or something. She was chasing me, crawling around, hiding behind the furniture, and laughing so hard,” Dean chuckled once, “God, it felt so real...”

“It _was_ real,” Cas smiled back, “It was a memory I pulled from your subconscious, Dean.”

Dean's grin softened to a meaningful look as he searched his husband's face. Holy shit. It really happened? Damn, Dean was glad that he was able to see it again so vividly... thanks to Cas. The man swallowed a bit before leaning forward to capture the angel's mouth. Dean put as much heart and soul into this kiss as possible, wanting to demonstrate just how much he appreciated and adored his husband. Cas responded immediately, cradling the side of Dean's face with one hand and placing his other over Dean's heart. With the cold wind ruffling the green grass all around them, Dean pulled back to rest his forehead against Cas's, savoring their shared breath.

“Cas. You're the best damn thing that's ever happened to me,” he whispered.

Cas's smile warmed every part of Dean's body, especially his heart.

“Dean, my love... I feel the same about you,” the angel hummed.

The two of them gazed into each others' eyes for a few more joyous moments before disappearing from the emerald hill, leaving the burning building far behind.

* * *

Things started to settle down once everyone got back to Bobby's house. Rowena had fallen asleep in the kitchen, sitting in a chair with her head tucked into her arms on the table, so Bobby carefully moved her to the sofa. Jude smiled when he saw Crowley helping Bobby arrange some pillows around her. It was nice to know that even though they bickered and fought all the time, Crowley and Rowena still loved each other very much. Ollie mentioned that he had about twenty missed calls on his phone – all from his mom – and asked Jessica to take him home. She agreed to fly him, and told Sam and Gabe that she would meet them back at the bunker when Ollie was safe. Uncle Sam, Gabe, Dad, and Papa told uncle Crowley that they were very happy that he was okay and to call if he needed anything. But before the four of them left for the bunker – and even though he knew he was an adult – Jude still pulled his parents aside and asked if he could stay the night with Clarence. Dad and Papa both agreed that it was a good idea, gave him hugs, and flew back home, leaving Jude at Clare's side.

That evening, Crowley mentioned needing to straighten up a few things in Hell and Bobby offered to go with him. With the two older men gone to another realm and Rowena asleep, Jude and Clarence basically had the whole house to themselves. But Clare, understandably, just wanted to get some sleep. Jude cuddled his fiance in bed that night, holding onto him gingerly and listening to his heartbeat, and waited for him to fall asleep. He wanted to make sure that Clarence got some real rest before he let himself go to sleep beside him. The only sounds in Bobby's house were the brief rustle of bedsheets, tiny snores, and the metronomic tick of the grandfather clock in the hall. The night was quiet, calm, and peaceful; the perfect setting to recharge batteries. And when Jude woke up in the morning, he felt loads better.

But just as it happened the morning before, Clarence was not in bed with Jude when the angel woke up. Jude blinked at the empty space and slowly raised his head to look around. Oh, no. Where had Clare gone to this time? Jude instinctively raised his left hand to make sure his engagement ring was still there – and it _was_ still there, glistening and shining back at him like twinkling stars – before rolling over to get out of bed. Clare wasn't in the room, but his bedroom door was cracked open, and Jude could hear voices coming from the hall. The angel crept closer to hear the quiet conversation outside.

“ - it has an almost endless shelf life, so you won't need to brew another batch anytime soon,” Crowley's accented voice said, “Why, boy? Are you planning to do something stupid?”

“No,” Clare instantly replied, “I swear. I was just curious.”

“You'd tell me if you were in trouble again, correct?” Crowley firmly pressed.

“Yes. I promise I was just wondering,” Clare assured again, “Are you sure _you're_ gonna be okay?”

Crowley scoffed loudly, as if he found the question offensive.

“I'm the bloody King of Hell. There isn't a single curse out there that could damage the essence of my grandeur,” Crowley purred, voice oozing with confidence.

Clare's chuckle echoed down the hallway and Jude smiled. It was good to know that Crowley hadn't lost any of his arrogance.

“I'm glad to hear it,” Clare replied, “Thanks, Crowley. I'm gonna go check on Jude.”

Jude gulped at the sound of his name. He didn't want to be caught eavesdropping on Clare and Crowley's conversation, but he knew he didn't have enough time to get back in bed and pretend to be asleep, either. Clare's footsteps were rapidly approaching. The only thing Jude could think to do was stand there like an idiot. Luckily, when Clare came back in and saw him, a smile spread on his lips.

“Mornin' Jay,” he sang, “How long have you been up?”

Jude smiled back at his fiance, but noticed a bottle in Clare's hands. It was a glass bottle with some kind of blueish white liquid inside, topped with a cork. It had to be a potion of some kind. Clare pecked a quick kiss to Jude's lips as he slid by to get to the dresser behind him. The demon sat the bottle down and dug around the clutter for a small piece of paper and a pen.

“J – just a few minutes,” Jude slowly answered, curiosity getting the best of him, “Clare, What's that?”

The demon didn't answer at first. He wrote something out on the paper, folded it up, picked up the bottle again, and turned back to Jude. Clare's green eyes seemed very awake this morning; full of life and _happiness_ that Jude hadn't seen there in so long.

“Jude, can you do me a favor?” he asked quietly.

Though he was still curious about the potion bottle and whatever Clare just wrote, Jude forced a nod.

“Sure,” he agreed.

“I know this is going to sound strange, but... Can you take me back to that crack house in New York?” Clare breathed.

Jude felt his own mouth open a little bit. What? Clare wanted to go back to that awful house? Where his _mom_ was? But why? The angel's eyes glanced toward the bottle in Clare's hands and he felt a little concerned. Was that bottle full of... poison? Was Clarence planning to kill her, just like the warlock wanted? The worry must have been visible on Jude's face, because Clare's expression turned a bit firmer.

“Please, Jay,” he added, “This is something I have to do.”

Jude was extremely apprehensive. He wasn't sure what Clare was going to do to Meg once they got there. Was he going to force her to drink the poison? Hurt her? Kill her in cold blood? If so, Jude didn't want to be a part of it... But somehow, looking up into Clare's open eyes made Jude reconsider. Jude would trust Clarence with his own life. Shouldn't the same apply to Meg? Though he was still leery, Jude reached out to take his fiance by the arm and closed his eyes, concentrating his grace to fly them back to the house in New York.

The flight, of course, was still a little rough for Jude. He had to combat the sickness in his stomach when they landed, which had formed from a mix of inertia and the sudden stench of the crack house. When he opened his eyes, Jude found that his grace had brought him exactly where he wanted to go. He and Clare were now standing in the same room from before... with Meg passed out on the mattress nearby. The window – the same that the warlock fell through – was now alight with the morning sun, casting lovely golden rays into the room. It was brighter here now, which only seemed to highlight Meg's terrible condition.

The female demon looked like nothing but skin and bone. Her hair, which looked like it hadn't been washed in quite some time, was laying thickly around her hollow face. Her mouth was slightly open and Jude almost thought she was already dead, but her chest was slowly rising and falling. She looked like a starved, exhausted, sickly creature... and it sadly reminded Jude of the first time he saw Clarence...

A few seconds after they arrived, Clare turned and walked over to shut the door behind them. He locked it too, and once Jude heard the click, his worry returned at full power. What in the world was Clare planning to do? Jude couldn't hold back his curiosity anymore.

“Clare, what are we doing here?” Jude finally asked.

The handsome demon took a large breath and finally faced Jude. He held up the blueish white potion and briefly pursed his lips together.

“Rowena brewed this for me. A long time ago,” he explained, looking down at the bottle in his hands, “It's a, um... detox agent. She said she made it in case I ever fell off the wagon and started using again. I told her she was crazy, because as long as I had you around, Jay, I'd never even look at drugs again.”

Jude nodded as he looked down at the bottle. He was overwhelmingly relieved that it wasn't poison. Clare gulped and nodded, seeming a little bashful all the sudden.

“And since _I_ don't need it...” he mumbled.

Clare didn't finish his sentence. Instead, he slowly walked back across the room. He brushed passed Jude to kneel down on the floor next to the dirty mattress. Clarence carefully placed the bottle on the floor next to the few burned out candles, shifting it to face the mattress. Then, he placed the piece of paper he wrote on next to it. Jude tip-toed close to read the message from above: ' _Meg. If you want to feel better, drink this._ ' Jude gulped. Holy crap. Clare was giving the potion to his mom. To make her feel better...

After he put the bottle down, Clarence paused to just look at her. His expression was kind of flat, like he was thinking about all kinds of things while he absorbed the sight of his real mother. Jude refused to interrupt the silence by asking questions. He just stood by his fiance's crouching form and waited patiently, watching him with admiration. A few moments passed by before Clare slowly dropped his hand. It started on the floor, slid across the mattress, and carefully picked up Meg's limp hand. The female demon didn't stir at all. She remained fully asleep as Clarence cradled her frail hand and held it in his own. He covered her fingers, blinked down at her, and took a deep breath.

“I forgive you...” Clare whispered.

Jude swallowed again, feeling tears press hard at the back of his eyeballs as he witnessed the scene take place. All this time, he had been thinking that Clare was going to hurt his mother, but no. He had come here to _forgive_ her; to give her some help and take her pain away. He was offering her a chance at a better life, even though she never gave him that option. Clare was wiping their slate clean and starting fresh. It was the single bravest act Jude had ever seen...

Though Meg wasn't awake to hear the message, Clare must have felt that it was delivered, because he laid her hand back down and stood up. The demon stared at his sick mother for a few more seconds before finally turning to look at Jude – where he made a weird face.

“Jay? Are you okay?” he asked.

Jude sniffled and quickly wiped his eyes, not wanting to seem childish in front of his fiancé.

“Uh, y – yeah. I'm just... really proud of you,” Jude admitted, smiling fondly at Clare.

The demon smiled back and stepped over to wrap both arms around the angel.

“Ready to go home?” he asked in Jude's ear.

Jude nodded and spared one more look at Meg and the bottle on the floor, before hugging his fiance tightly and letting his grace work. His wings rustled once and flew them back to the safe, sweet-smelling harbor of Clare's room. They were only gone for a few minutes, but it felt like so much longer. Even when they arrived, Jude didn't let go of Clare. He kept clinging to his favorite demon, nestling his head on Clare's shoulder and smiling sideways at his face.

“I'm going to marry the hell out of you,” Jude hummed, his heart fluttering in his chest.

Clare chuckled again, delighting Jude's ears with the lovely sound. The demon tilted his head to peck another kiss to Jude's smiling lips.

“Not if I marry you first,” he replied with a wink.

 

**Notes for the Chapter:**

> Ladies and Gents, I'm proud to say the transformation is complete. Clarence is no longer a lost boy. He's officially a full grown, sound minded adult in all aspects of his life. Thanks to the Winchesters, Clare is gonna be a very happy camper from here on out. No more angst for him! :) In fact, his actions at the end of this chapter will impact the rest of the story. As in, (* **spoiler alert, skip ahead if you don't want to read** *) Meg will eventually return as her lovely, badass, canon self. (* **End spoiler** *) :D I really hope you guys stick around to see how that pans out because I think it will be amazing. :) I have to admit that Dean's convo with Clare was partially inspired by the book, “The Shack.” (I cried all the way through that one. Make sure you have tissues handy if you give it a read. Lol) ;) Also, I hope that I didn't take too much liberty with Dean's childhood, by saying that he never had a good dream about Mary except when Cas gave him one. I just figured that seeing her burn on the ceiling was so traumatic that it would scar him that way for a long time. And I know that this seems like the last chapter, but it's not. There is still one more chapter to go for this part, and I really hope you all stick around to see it next week! :D Thank you all soooo much for reading and commenting! I couldn't ask for better readers! You are all beautiful blessings to me! *hugs* The next chapter will be out soon! :)


	13. Chapter 13

Sam carefully scooped all of the books out of Crowley's arms, sneaking close and studious glances at the demon's face in the process. It had been almost twenty-four hours since the curse on him was broken, but Sam was worried that there could have been some lasting effects. Seeing Crowley's body trying to melt into black goo was traumatizing, to say the least. Surely, a curse as powerful as that would have left some kind of mark. Even if it was just mental and emotional scarring... But in true 'King of Hell' fashion, Crowley seemed to have effortlessly bounced back to his smug, arrogant, sassy self.

“Are these _really_ all the books you have on magical beings?” the demon droned, “An entire bunker of libraries and lore, and you've only got a handful of volumes detailing magical beings. Bit pathetic, isn't it?”

“We didn't stock the bunker, Crowley. It was all in place when we got here,” Sam sighed with a smirk, “You and Rowena have been spoiled by Bobby's collection.”

“Yeah,” Gabe added over his shoulder from across the room as he slid a few books back on a shelf, “It's not our fault that you and the Scottish Shrew get to raid Singer's legendary stash whenever you want.”

Crowley blinked his dark eyes away and tilted his head toward Bobby, who shrugged his shoulders and smiled.

“Kids've got a point,” he muttered, winking subtly.

The conversation paused while everyone else finished re-shelving the books in their hands. Sam, Gabe, Dean, Cas, Bobby, and Crowley were all in the study, quietly tidying the place back up and putting their borrowed books back. Jessica was still asleep in her room, while Jude was with Clarence back at Bobby's house. Sam was a little uncomfortable with the silence. Even though he was home and surrounded by most of his family, there was still this sinking feeling that he couldn't get rid of. It was almost like he was expecting something else to happen; the warlock to come back, or Crowley to suddenly get sick again. Sam knew it was probably just a case of paranoid worry, but he couldn't convince himself that nothing was wrong.

“Are you sure you're gonna be alright, Crowley?” Dean asked quietly.

From the tone of his brother's voice, Sam knew that Dean must have been feeling the same way he did. Sam shelved his last book and turned around just in time to see Crowley forcefully roll his eyes.

“If any of you ask me that damn question again...” he growled, briefly pinching the bridge of his nose, “Yes, okay? I'm fine. Bloody brilliant. As plump and merry as Father Christmas. Alright? Happy now?”

Sam shared a few glances with his brother, brother-in-law, and husband, who all seemed equally offended by Crowley's outburst. Sheesh, they were just worried about him. There was no need to bit their heads off. Bobby seemed to understand the Winchesters' point of view because he walked over to run his hand against the back of Crowley's suit.

“Lighten up, darlin'. They just care about you,” he muttered lowly, probably only for Crowley's ears.

The demon stared at the old hunter for a second and Sam could see a tiny hint of tenderness seep into Crowley's hard expression. His dark eyes loosened their scowl and he blinked softly up at Bobby. After a moment of pondering his thoughts, Crowley took a deep breath.

“I know,” the demon grumbled.

Crowley turned to face the other four men in the study, raising his head up higher to look among them all. But Sam noticed that he stuck his hands in his suit pockets, as if hiding nervous, jittery fingers.

“As usual, my darling husband has provoked me to voice my thoughts,” he began, voice still low but much more gentle, “I... I'm grateful to all of you for your assistance. If it weren't for your signature quick thinking, selfless bravery, focused determination, and unbreakable willpower... I simply wouldn't be standing in this room with you.”

Sam smiled a little and spared a glance at Gabe. The archangel was already looking back at him, puppy eyes at full power. Gabe casually slipped over to curl an arm around Sam's lower back as they listened to Crowley speak.

“Believe me when I say that just uttering the words 'thank you' would be an insult to your heroic actions,” the demon continued, sounding kind of ashamed, “In fact, I... I hardly deserved to be on the receiving end of them at all... It boggles my mind that you would fight so courageously for my life, when it has only brought pain and suffering to many others -”

“Crowley -”

“No, Robert, don't interrupt,” Crowley silenced Bobby's outburst with a raised hand, “It's true. We all know how evil I am.”

“As evil as a fat house cat,” Gabriel whispered to Sam.

Sam bit down a chuckle, but kept his attention on Crowley.

“The point is that my life wasn't worth the battle you fought this week,” the demon added, “But you fought for it anyway. And for that, I am incomprehensibly speechless. I don't deserve your care. Your sympathy... Your... _love_ ,” he hissed, “... but I am very grateful to each of you. Especially the children. I never expected that I would ever be thought of as... as... ”

“Family?” Dean finished with a smirk.

Crowley gulped.

“Yes. Family,” he nodded, “So, as mundane and pathetic as it is to say... Thank you. All of you. For giving me more time to be a part of this family. I promise to be the best brother, uncle, husband... and father... that I can be.”

Sam's smile grew as he tightened his arm around Gabe. It was so sweet to hear Crowley talk so openly and sincerely. After Crowley's little speech, Bobby patted his shoulder and grinned.

“Aww. That's sweet, darlin,” he hummed, “You want some tissues? Need me to play ya a song on the world's smallest violin?”

All the men chuckled when Crowley's glare returned at full power.

“You're a riot, dear. A true comedian,” he said blandly, “Are you ready to go home, or shall I leave you here to think about what you've said?”

“Ah, you know I'm just teasin',” Bobby said, pulling Crowley close to peck a kiss to his temple, “'course I'm proud of you. And you _are_ worth the fight. Right fellas?”

“Absolutely,” Cas immediately agreed, “Our family would not be complete without you, Crowley.”

“Yeah. You're like the weird uncle that everyone avoids at family gatherings,” Gabe winked.

Crowley sighed and rolled his eyes dramatically, though he seemed more amused than offended.

“Sorry, man. Ball busting is part of being a hunter,” Dean added.

“I'm fondly aware,” Crowley nodded, glancing around again, “but still. Thank you all for saving my life... Now, if you'll excuse us, Robert and I have some affairs to tend to at home. Don't we, love?”

“Yep. Gotta replant all that Kingsfoil in the garden and fix that portal,” Bobby nodded, searching among the Winchesters, “You boys done real good this week. I'm mighty proud of all of you.”

“Thanks, Bobby,” Sam offered for everyone, sharing a smile with him.

Crowley reached over, casually wrapped an arm around Bobby, and paused to give everyone else in the room one more thankful smile before the two of them disappeared in a puff of black smoke. Sam blinked at the spot they had been standing in and continued to smile. It was so nice to hear Crowley – the king of all demons – talk about love and family so sweetly. The guy had a hard exterior but a gooey center. He and Bobby had more in common than Sam thought...

“What a week,” Dean sighed, walking over to half-sit on a table and rub his forehead with his palm, “I say we all sleep in tomorrow. Deal?”

“Deal. I've got a lot of moose-time to catch up on,” Gabe agreed, squeezing Sam closer to his side.

“I am very proud of the children for defeating the warlock on their own. When it comes to bravery, I believe Jude and Jessica take after their fathers,” Cas mused, stepping over to affectionately rake his hand through Dean's hair.

“Hell yeah they do,” Gabe agreed, turning to look up at Sam, “Our daughter blasted a warlock to pieces, Sammy. _Our baby rabbit_! Seems like only yesterday that she was running around in diapers, and now she's mercilessly slaughtering evildoers. They grow up so fast...”

Sam gulped hard. He knew that Gabe's comment was meant to be humorous, but it somehow struck Sam as heartbreaking, too. It really _was_ only yesterday that Jessica was a little baby; just learning to walk, and talk, and play tea party with Dickie. Where had the time gone? And why couldn't it come back?

“I'm proud of them, too,” Dean nodded against Cas's cradled hand, “but I've gotta tell you guys, I'm a little worried about this whole 'Death' thing.”

Sam's jaw nearly dropped. That was it. Dean just pinpointed Sam's feelings exactly. The 'Death' thing was the reason why he was so nervous on the inside, too.

“Worried? Why?” Gabriel asked.

“Because it's _Death_ ,” Sam said, hoping to point out the obvious, “We can't just kill Death without repercussions, can we?”

“No, you can't.”

All four men jumped up at the sound of a new voice. It came from the other end of the room and echoed against the shelves. The tone was loud, firm – and distinctly _feminine_. Sam spun around to search for the source and found a brand new face. There, standing in front of the telescope at the end of the study, was a lovely cocoa-skinned woman in a black leather jacket. Her arms were crossed and she was staring down the four men in the room with hawk-like eyes. All of the Winchesters slowly turned to face her in a line, starting with Dean and ending with Sam. Sam was at a loss. Who was this woman? And how did she get into the bunker?

“Who the hell are you?” Dean barked, his tone harsh and full of warning.

The lady shifted her eyes to him without moving.

“Funny thing,” she said humorlessly, “My name's Billie. But now, I have a new title. So you can call me... Death.”

Sam's mouth fell open. What? _She_ was Death? But how could that be? No, that old, British horseman they killed, _he_ was Death. Right?

“How?” Cas asked, his stance just as defensive as Dean's.

“Of course an angel like you wouldn't understand how it works,” she judged severely, appraising him with disgust, “I'm a reaper. You killed Death. I took his place. Now, I have all the same power he did, only this time – ”

The lady paused to uncross her arms and reached for the air next to her, where a scythe materialized in her grasp. The weapon was taller than her by a foot and looked much different from the one they used on the original Death.

“It's got a little more kick,” she finished.

“Easy there, miss kitty,” Gabriel said, holding his hands up in surrender, “I don't know why you're here, but -”

“I'm here to give you a warning,” Billie interrupted, her dark eyes glowing feverishly, “The guy who had this job first might have let you run all over him, but it won't be that way with me. I'm in charge now, and I plan to keep this job for a looong time,” she purred without a trace of humor as she eyed each one of them carefully, “You Winchesters have gotten cocky. You think that death won't apply to you, but it will. Everything that lives must die, including each of you... but until that time, let's agree to keep this relationship professional. I have a job and you have a job. As long as you keep your business out of mine, we'll be okay. But the minute you cross that line, the gloves are coming off and the scythe is coming out. Are we clear?”

No one said a word. Everyone was too stunned and mesmerized by Billie's dominant tone to properly speak. But she seemed to take the lack of response for defiance. Her eyes cut to the oldest Winchester.

“I said _are we clear_ , Dean Winchester?” she barked.

“Y – yes,” Dean breathed with a nod, “Crystal.”

“Good,” she replied.

Billie allowed the scythe to disappear from her hand before crossing her arms again. She slowly swiveled her head to look around, causing her curly black hair to spin with it.

“Don't make me come back here, boys,” she requested firmly, “You're all handsome as hell, but I don't want to see your faces again any time soon.”

Sam nodded along with his brothers and husband, taking the odd compliment in stride with the warning. With her statement spoken, Death disappeared from the room, leaving all four Winchesters with open mouths and large eyes. Sam wasn't sure what to say. He thought that Death was one person, not a title. But it made sense that 'Death' was a job that needed constantly filled. The lady playing the part now was difficult to read for sure.

“She seems... nice,” Gabriel attempted.

“It sounded as though she did not want a feud with us,” Cas pointed out, “Only our cooperation.”

“Well, she can obviously get into the bunker whenever she wants. I say we try to stay on her good side,” Dean grumbled, sounding a little offended that someone outside of their family could get into their house so easily.

Sam opened his mouth to add something about reapers taking each others' places as Death, when his phone started ringing. He shifted around to grab the cell out of his pocket and held it up to see who was calling. Oliver Thompson's name was on the screen, but instead of feeling annoyed as usual that he was calling, Sam felt kind of eager. He actually wanted to know how the kid was doing now that they were all back home. Sam swiped the answer button and held the phone to his ear.

“Hello?” he asked.

“S – Sam?” Oliver replied.

From the moment the kid spoke, Sam could hear the fear in his voice. For some reason, Oliver sounded absolutely terrified. But why? Did something happen?

“Yeah. Is everything okay?” Sam prompted.

“I... I need your help,” Ollie breathed, voice shaky, “Please...”

* * *

Jessica rolled over in bed, curling on her right side to gaze blandly at her vanity table across the room. She had no idea what time it was, but she had been awake for at least ten minutes now; laying there, thinking about things. It wasn't until she tallied the week's events in her mind that she realized just how upset she was. Almost nothing had been pleasant for anyone over the past few days. Crowley went through so much pain, Clarence was emotionally damaged, Ollie was upset over dropping out of school, and her dads were forced to kill Death itself. It was like being trapped in a family drama movie that wouldn't end.

But Jess couldn't deny that some good things had happened too. She got to go back in time and meet her Grandpa John, which was something that she always wanted to do. She comforted her boyfriend after he broke the news that he had dropped out of school. And she was finally able to kill the warlock and put an end to both Crowley and Clare's suffering, helping everyone along the way. But despite all those good things, Jessica still felt like crap and she didn't know why. She had absolutely no reason to feel sad, but there she was; sulking in bed. Maybe it was some of the leftover guilt she felt when uncle Crowley got hurt. After all, it was her fault for not killing the warlock when she first had the chance. Maybe if she had killed him sooner, she could have spared everyone all the heartache...

As she laid in bed, Jessica felt some of her blankets move near her feet. With furrowed eyebrows, she leaned back on the bed to see the disturbance and found Dickie sniffing around. Seeing the adorable dog actually made her feel better instantly. She had missed him and his calming affects this week.

“Hey, Dickie,” she smiled a little, lifting her arm up, “Come here.”

At the call, Dickie instantly sprinted down the bed to nuzzle his way under Jess's arm. He crawled up to lick her face and she shook her head away with a giggle. He had terrible smelling breath.

“You need to brush your teeth,” she mentioned playfully.

Dickie only tilted his head, making his ears flop adorably. The two of them snuggled for a moment – until a prayer suddenly sounded in Jess's mind. She paused her petting hand on Dickie's head to listen to the voice; her dad's voice.

' _Jess, come to the control room._ '

Jessica looked down to give Dickie a weird look. Huh. That was strange. Dad hardly ever prayed to Jessie like that. He usually just walked to her room to ask her questions. Maybe something important was going on. Jess sat up on her bed, stretched her arms, gave Dickie's head a quick kiss, and got up to start through the bunker. She was still wearing her PJs – a Bugs Bunny t-shirt and fuzzy, daisy print pants – but hoped that it would be a suitable outfit for whatever was going on in the control room. Hopefully, they had just moved breakfast in there or something.

Unfortunately, when Jess got there, she was met with a worrying sight. Dad, Papa, and Ollie were all standing around the map table with pale faces. They were looking down at something on the table, but raised their heads to her when she entered. All of them seemed scared for some reason, lips turned downward and eyebrows curved.

“Wh – what's going on?” Jess asked.

“Oliver found this on his doorstep this morning,” Dad explained, pointing toward the table, “We think its some sort of puzzle or ransom note or something, but we can't figure it out.”

Jessica's heart dropped as she stepped up to look down at the table, realizing that the surface was covered with scattered magazine letters. Was it really a ransom note? Who would have done that? Who would leave some kind of threatening message on Ollie's doorstep? Jessica raised her eyes to look at her boyfriend and found that he was paler than she had ever seen him before. He looked downright terrified. When they met eyes, Ollie gestured toward the pieces.

“C – can you figure it out, Jess?” he urged, voice shaky, “I just... I can't figure it out.”

Jessica gulped and looked to her parents, who also looked scared. Oh, no, who was behind this? Did they want to hurt someone? Were they targeting Ollie and his mom?! Needing answers, Jess quickly rounded the table to wedge herself between Dad and Ollie. Dad pointed toward the pile of magazine letters, sliding some out to line them up.

“We're pretty sure that there are four words,” he estimated.

Jessica looked down at the starting letters, 'W', 'Y', 'M', and 'M'. There were ten others, and a lot of them were vowels. Jess started with those, sliding them into each of the slots to figure out what kind of words they would make. She cycled through many different words – wear, woe, mule, year, yale, more – but none of them made any sense. The longer she tried to figure it out, the more frustrated she became. If someone was going to leave a warning or ransom note, why would they make the victim figure it out? To scare them even more or something?

“It's not making sense,” Jess grumbled nervously.

“What about 'Willy'? Maybe they're talking about Bobby's dog,” Papa suggested.

“Gabe, that's dumb,” Dad sighed, “but the first word might be 'Will.”

Jessica quickly arranged the letters into 'Will' to see what it would leave. Seven letters, including four vowels, and absolutely no hints. Jess frantically kept arranging with no idea what the message was saying.

“Yoyo,” Papa said, “The next one is definitely yoyo!”

“Gabriel, there is only one 'O',” Dad snapped.

“Wh – what about 'you'?” Ollie timidly suggested, swiping the back of his hand across his forehead before backing up.

Jessica went with her boyfriend's suggestion and arranged the letters accordingly. Afterward, she was left with five more letters. The other two words couldn't have been very big. Feeling a bit panicked, Jessica used her fingers to switch around every combination that she could think of. She accidentally ripped one of the 'R's in the process. It wasn't until Dad reached over and moved just one of the letters that Jessica finally got the full message. She and Papa both lowered their heads to read the strange message before them.

_Will... you... marry... me..._

Jessica and her Papa both gasped and covered their mouths at the same time. Marry?! Wait a second, what did that mean? _Was some other girl asking Ollie to marry her_?! Jessica spun around to ask her boyfriend about it – but found him kneeling down on the floor behind her. He was on one knee, face so pale that his freckles were faded too, and he was holding up a tiny open box in his hand. The box was shaking so much that she could barely see the sparkly object inside. Jessica could feel her own eyes watering as she blinked down at her boyfriend in shock. This was it. It was really happening. _Oliver was finally going to ask the question._

“ _Holy shit!_ ” Papa squeaked behind his hands.

Dad reached over to shush Papa with a grin, but Papa's brief interruption seemed to distract Ollie for a second. He gulped hard and lowered his head, his pale cheeks turning a little pink, probably because he didn't like the added attention of Jess's parents being in the room. But his cocoa eyes soon found Jess's again and he was able to regain some courage.

“I... I know this is s – super overdue,” he said so quietly that Jess could barely hear him over her own thumping heart, “but I wanted to surprise you because... because you deserve a few good surprises every now and then.”

Jess giggled behind her hands. It was louder than she intended, but she couldn't help herself. She had waited for this moment since she was a little girl. Ollie gulped again and continued.

“Jess, you – you're amazing,” he kept going, struggling for words, “You are so sweet, and funny, and beautiful, and brave. You can fly around and punch warlocks in the face, and its so cool... and kind of scary...”

Jess giggled again, curling her hands together to tuck them under her chin as she stared down at her true love. He was being his perfectly awkward and sweet self, which was just what she wanted. Ollie paused again and his nervous smile faded into a more serious – and even more terrified – look.

“I was a – afraid to ask you this,” he admitted, voice shaking almost as much as his hands, “because I... I didn't want us to end up like my parents... but then I realized that we are more like _your_ parents than mine -”

“ _He's talking about us, Sam!_ ” Jessica could hear her Papa's voice whispering excitedly to her Dad.

“We are just like them. N – not because we are gay or anything, I mean,” Ollie revised, his eyes widening as he glanced toward Dad and Papa, “Not that being gay is a bad thing! It's not bad! I – I just mean that... ugh...” Ollie sighed and looked back to Jess, who was holding down more giggles, “I just... I meant that we love each other like they love each other. We're always together. Laughing, and watching movies, and playing pranks, and talking about everything... You've always been there for me, as long as I can remember. I literally grew up right next to you... And that's where I always want to be.”

Jessica's heart melted in her chest as tears streamed down her face. Ollie adjusted the small box in his grasp, using both hands to hold it steady. Jessica was finally able to see the beautiful engagement ring inside, but Ollie's emotion-filled face was too handsome to ignore. She stared down into his eyes as he said his next words.

“Jessie, y – you've always been my angel,” he said softly, “... Will you... Will you be my wife, too?”

“ _Yes!_ ” Papa shouted.

Jessica and Ollie both looked toward her parents, seeing Papa's eyes widen in shock. Obviously, he didn't realize that he had answered for Jessica until just now. Next to him, Dad shook his head and rolled his eyes.

“See, Gabe, _this_ is why we can't have nice things,” Dad hissed.

“I'm sorry!” Papa groaned, turning back to Jess and Ollie with shooing hands, “Go on, baby rabbit. I didn't mean to say that out loud. You answer him.”

Still wearing a smile, Jess returned her attention back to the ginger-haired dream kneeling on the floor before her. Ollie's brown eyes found their way back to hers and she made sure he would be able to hear the honesty in her voice when she spoke again.

“Yes,” she breathed, finally releasing the answer that had been dying to get out of her mouth all week, “Absolutely _yes_.”

A giant, beautiful smile of relief spread across Ollie's cute face and he took a deep breath. While Papa cheered vigorously in the background and Jessica tried to contain her own happy tears, Ollie climbed up from the floor and took the ring out of the box. Jess offered her left hand, but Ollie's were so shaky that he barely managed to get the ring on her finger. As soon as it was placed on her, though, Jessica took the time to appraise it. The thin band was gold, and topped with a big, beautiful, perfectly round Opal. Several tiny diamonds formed a circle around it, outlining the shimmery gem. The magical Opal reminded her of mermaid scales – or unicorn eyes – and was very familiar. She had seen this ring on her own finger in lots of her future dreams, and it was going to stay there for the rest of her life...

“I'm sorry I couldn't afford a big diamond,” Ollie mumbled, sounding ashamed, “But this one was really pretty and I thought that you might like it. We can go back to the store and get a diff -”

“No!” Jess croaked, shaking her head as she tossed both arms around her boyfriend's large shoulders, “Ollie, it's _perfect_. I _love_ it... Almost as much as I love you.”

Ollie's blush made Jessica's smile widen. She stared at him for another moment before capturing his pink lips for a kiss. While their mouths met and tongues danced, Jess could feel Ollie's arms wrapping gently around her back. Suddenly and all at once, Jess's worries faded away. As long as she was there – inside the arms of the man she loved most in the world – it felt like nothing bad could ever get to her. Everything as going to be alright as long as Ollie was by her side. And the new ring on her finger was proof that it was going to stay that way forever.

“I love you, too,” Ollie pulled back to whisper, his smile dimming, “and I really am sorry it took so long.”

“Don't be,” Jess assured, brushing some of his pumpkin-colored hair out of the way, “It was well worth the wait.”

Ollie's smile returned at full power and it made Jess's stomach flutter.

“My baby bunny is getting married! Oh my Dad, there is just so much to do!” Papa said, tugging on Dad's arm, “Sammy, we've got to find a good venue! And help her pick out a dress! And get the cake! And send out invitations! Holy crap, _Jane doesn't even know yet! We have to tell her!_ ”

“Gabriel, _shhh_ ,” Dad said, cupping his hand around Papa's mouth, “Let the kids tell Jane, okay? We'll figure out everything else later. They don't have to get married right away. They can take their time, right guys?”

When Dad looked to her and Ollie, Jessica glanced to her fiance's large cocoa eyes. Ollie seemed nervous again, probably because of the mention of a wedding. But he nodded frantically when Dad spoke.

“Y – yeah,” he replied, “I mean, Mom will probably want to help with stuff, too. And I... I have a lot of family to invite. Like, _a lot_...”

“That's okay, carrot-top. The more the merrier!” Papa rejoiced, suddenly gasping, “ _Oh!_ We have to tell Cassie and Deano! C'mon, Moose!”

Before Dad could even open his mouth to protest, Papa grabbed his arm and flew away; disappearing from the room and leaving Ollie and Jess alone. Jess giggled at her parents' delight before her eyes dropped to the paper on the map table. The words 'Will you marry me' were still situated on the page, staring back at her with subtle enthusiasm. In her mind, Jessica already decided that she was going to glue the magazine letters to the page and keep it forever, as a physical memory of when her future husband asked her to marry him... Jess sighed blissfully as she tightened her arms around Ollie's shoulders and blinked back at him.

“We've got a lot of milestones ahead of us, Ollie-pop,” she predicted with a smirk.

Ollie smiled back, making the adorable freckles stretch on his cheeks.

“I can't wait to see them all with you,” he replied softly.

 

**Notes for the Chapter:**

> Yaaay! Ollie finally popped that question! It's a Christmas miracle! XD I hope that his method of using a 'ransom' note wasn't too out there. He just really wanted to throw Jessie off the scent. And, in case it wasn't clear, Sam was totally in on it the whole time, which is why he nudged her in the right direction with the words. ;) I hope that Crowley's emotional thank you speech wasn't too out of character. (The Winchesters just give him feels. Lol) and I hope that you guys like the addition of Death 2.0! I do love Billie's character, and might even use her again in the future. :) As you all are probably aware, **there will be another part coming soon!** :D I am super excited to write this one because there is going to be nothing but fluff and humor and smut in it! As in, no real angst, no bad guys, no life or death situations, no violent drama. Just good old fashioned fun stuff! I promise :) (I think we all need a good dose of that. Lol.) :D I'm not sure when exactly the new chapters will start rolling out, (probably some time around the beginning of January,) but until then, I wish you all a Merry Christmas and Happy Holidays! :D Each and every one of you has been my biggest blessing of 2018, and I cannot wait to offer you more entertainment next year! :D Thank you so much for reading and commenting! Have a blessed season! :)


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